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Here is a chemical reaction formula: Reactants are m3_m4:C(CN)N, amount is: 0.0 ;m3_m4:O, amount is: 0.0 ;m1_m2_m5:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)Br)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m2_m5:C(#N)[Cu], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C#N)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 4-[3-(2-benzyloxy-5-bromophenyl)propyl]-benzoate (0.5 g) and CuCN (250 mg) in DMF (20 ml) was heated at reflux for 18 hours, poured into ethylene diamine (20 ml) and water (60 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with brine (100 ml), dried (magnesium sulphate), filtered and evaporated to give methyl 4-[3-(2-benzyloxy-5-cyanophenyl)propyl]-benzoate (290 mg). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)CO)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m3_m2:CC1=CC=C(C=C1)S(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)COC)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of methyl 4-[3-(2-benzyloxy-5-hydroxymethylphenyl) propyl]benzoate (5.31 g) in methanol (100 ml) was added 4-methylbenzenesulphonic acid (3.11 g). The reaction was heated at reflux for 18 hours, the solvent evaporated, the residue dissolved in EtOAc, washed with brine and the solvent evaporated to give methyl 4-[3-(2-benzyloxy-5-methoxymethylphenyl)propyl]benzoate (3.64 g). |
Here is a chemical reaction formula: Reactants are m1_m5:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)N)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m4:CCOC(=O)C, amount is: 0.0 MOLE;m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m2_m3:ICC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)N(CC)CC)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of methyl 4-[3-(2-benzyloxy-5-aminophenyl) propyl]benzoate (250 mg) in DMF (5 ml) was added potassium carbonate (0.2 g) and iodoethane (0.16 ml). The reaction was stirred for 18 hours, diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography to give the methyl 4-[3-(2-benzyloxy-5-(diethylamino) phenyl)propyl]benzoate as an oil (150 mg). |
Here is a chemical reaction formula: Reactants are m1_m4:OC1=C(C=O)C=C(C=C1)O, amount is: 0.0 ;m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m2_m3:C(C(C)(C)C)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=C(C=O)C=C(C=C1)OC(=O)C(C)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 2,5-dihydroxybenzaldehyde (10 g) in dichloromethane (50 ml) at 0° C. was added triethylamine (5 ml) and pivaloyl chloride (4.4 ml). The mixture was stirred at room temperature for 18 hours, filtered and the filtrates washed with 2M HCl (100 ml), brine (100 ml) and sodium bicarbonate (100 m), dried (magnesium sulphate) filtered and evaporated. The residue was purified by chromatography on silica gel using dichloromethane:hexane (0:1 to 1:1 gradient) then ethyl acetate:hexane (1:9 to 3:7 gradient) as eluants to give 2-hydroxy-5-(t-butylcarbonyloxy)benzaldehyde (4 g) and some 2,5-dihydroxy-benzaldehyde. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)O)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 MOLE;m0_m1:FC=1C=C(C(=O)O)C=CC1C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:FC=1C=C(C(=O)OC)C=CC1C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 3-fluoro-4-methylbenzoate was prepared from 3-fluoro-4-methylbenzoic acid by the process described in Example 6 for the synthesis of methyl 4-(3-(2-benzyloxy-5-hydroxyphenyl)propyl]-benzoate. |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:FC=1C=C(C(=O)OC)C=CC1C, amount is: 0.0 ;m1_m2_m5_m3:BrN1C(CCC1=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5_m3:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 MOLE,Catalysts are m1_m2_m5_m3:CC(C)(C#N)N=NC(C)(C)C#N, amount is: 0.0 ;m4:[W], amount is: 0.0 MOLE.Products are 0:FC=1C=C(C(=O)OC)C=CC1CBr, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 3-fluoro-4-methylbenzoate (4.3 g), N-bromosuccinimide (4.5 g) and AIBN (20 mg) in carbon tetrachloride was irradiated with a 100 W Tungsten lamp at reflux for 1 hour. The mixture was filtered through diatomaceous earth, and evaporated to give methyl 3-fluoro-4-(bromomethyl)benzoate (5.0 g). |
Here is a chemical reaction formula: Reactants are m3:OC1=C(C=CC=C1)C(CCC1=CC=C(C(=O)OC)C=C1)=C=O, amount is: 0.0 MOLE;m2:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(/C=C/C1=CC=C(C(=O)[O-])C=C1)=C=O, amount is: 0.0 MOLE;m0_m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=CC1=C(C=C(C(=O)OC)C=C1)F, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C(C)O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:OC1=C(C=CC=C1)CCC1=C(C=C(C(=O)OC)C=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(2-hydroxyphenyl)ethyl]-3-fluorobenzoate was synthesised from methyl 4-(2-(2-benzyloxyphenyl) ethenyl]-3-fluorobenzoate using the hydrogenation method described in Example 1 (for the conversion of 4-[3-(2-benzyloxyphenyl)-3-carbonyl-1(E)-propenyl]-benzoate to methyl 4-[3-(2-hydroxyphenyl)-3-carbonylpropyl)benzoate but using ethanol as the reaction solvent). |
Here is a chemical reaction formula: Reactants are m0_m1:[N+](=O)([O-])C=1C=C(C(=O)O)C=CC1C, amount is: 0.0 MOLE;m2:FC=1C=C(C(=O)O)C=CC1C, amount is: 0.0 MOLE;m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=CC1=C(C=C(C(=O)OC)C=C1)F, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=CC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(2-benzyloxyphenyl)ethenyl]-3-nitrobenzoate was prepared from 3-nitro-4-methylbenzoic acid using the methods described in Example 8 for the conversion of 3-fluoro-4-methylbenzoic acid to methyl 4-[2-(2-benzyloxyphenyl)ethenyl]-3-fluorobenzoate. |
Here is a chemical reaction formula: Reactants are m0_m1:OC1=C(C(=O)O)C=CC(=C1)C, amount is: 0.0 MOLE;m2:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)O)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:OC1=C(C(=O)OC)C=CC(=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 2-hydroxy-4-methylbenzoate was prepared from 2-hydroxy-4-methylbenzoic acid by the process described in Example 6 for the synthesis of methyl 4-(3-(2-benzyloxy-5-hydroxyphenyl)propyl]-benzoate. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCC1=C(C=C(C(=O)OC)C=C1)N, amount is: 0.0 MOLE;m0_m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C=C/C1=CC(=C(C(=O)O)C=C1)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCC1=CC(=C(C(=O)OC)C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(2-benzyloxyphenyl)ethyl]-2-hydroxybenzoate was prepared from a Z/E mixture of methyl 4-[2-(2-benzyloxyphenyl)-ethenyl]-2-hydroxybenzoate (prepared as described in Example 10) using the hydrogenation method described in Example 10 for the synthesis of methyl 4-[2-(2-benzyloxyphenyl)ethyl]-3-aminobenzoate. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C=C/C1=CC(=C(C(=O)OC)C=C1)OC, amount is: 0.0 MOLE;m0_m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCC1=CC(=C(C(=O)OC)C=C1)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(2-benzyloxyphenyl)ethyl]-2-methoxybenzoate was prepared from methyl 4-[2-(2-benzyloxyphenyl)ethyl]-2-hydroxybenzoate (prepared as described in Example 14) using the method described in Example 14 for the preparation of methyl 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-methoxybenzoate. |
Here is a chemical reaction formula: Reactants are m0_m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CC=CC1=CC(=C(C(=O)OC)C=C1)O, amount is: 0.0 MOLE;m2_m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCC1=C(C=C(C(=O)OC)C=C1)N, amount is: 0.0 MOLE;m2_m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=CC1=C(C=C(C(=O)OC)C=C1)[N+](=O)[O-], amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC(=C(C(=O)OC)C=C1)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(2-benzyloxyphenyl)propyl]-2-hydroxybenzoate was prepared from methyl 4-[3-(2-benzyloxyphenyl)propenyl]-2-hydroxybenzoate by the method described in Example 9 for the synthesis of methyl 4-[2-(2-benzyloxyphenyl)ethyl]-3-aminobenzoate from methyl 4-[2-(2-benzyloxyphenyl)ethenyl]-3-nitrobenzoate. |
Here is a chemical reaction formula: Reactants are m0_m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC(=C(C(=O)OC)C=C1)O, amount is: 0.0 MOLE;m2_m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C=C/C1=CC(=C(C(=O)OC)C=C1)OC, amount is: 0.0 MOLE;m2_m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C=C/C1=CC(=C(C(=O)OC)C=C1)O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC(=C(C(=O)OC)C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(2-benzyloxyphenyl)-propyl]-2-methoxybenzoate was synthesised from methyl 4-[3-(2-benzyloxyphenyl)-propyl]-2-hydroxybenzoate (prepared as described in Example 15) as described in Example 14 for the synthesis of methyl 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-methoxybenzoate from methyl 4-[2-(2-benzyloxyphenyl)-(E)-ethenyl]-2-hydroxybenzoate. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC(C(=O)OC(C(F)(F)F)=O)(F)F, amount is: 0.0 ;m1_m2_m3_m4:C(C1=CC=CC=C1)OC1=C(CCC2=C(C=C(C(=O)N)C=C2)Br)C=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C1CCOC1, amount is: 0.0 MOLE;m5:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CCC2=C(C=C(C#N)C=C2)Br)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Trifluoroacetic anhydride (0.75 ml) was added to a mixture of 4-[2-benzyloxyphenethyl]-3-bromobenzamide (1.46 g) and pyridine (0.86 ml) in THF at -20° C. The mixture was stirred at ambient temperature for 18 hours, diluted with ethyl acetate and washed with water, dried (MgSO4), filtered and evaporated to dryness. The resulting residue was purified by MPLC on silica gel, eluting with CH2Cl2 to give 4-[2-benzyloxyphenethyl]-3-bromobenzonitrile as a white solid (1.34 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC1=C(C=CC(=C1)OC)CCCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m3_m2:[C-]#N.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CS(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC(=C1)O)CCCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-[3-(2-benzyloxy-4-methoxyphenyl)-propyl]benzoic acid (0.75 g) in DMSO (20 ml) was added sodium cyanide (0.5 g). The reaction mixture was heated at 190° C. for 40 hours, cooled, partitioned between 1N aqueous NaOH and diethyl ether. The aqueous layer was separated, acidified to pH1 (conc. HCl) and extracted with ethyl acetate. The organic solution was dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica gel eluting with diethyl ether, and crystallisation from CH2Cl2 /hexane mixtures to give the title compound (150 mg). |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C(C1=CC=CC=C1)OC=1C(=CC=2CCCCC2C1)CCCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m4_m2_m3:O, amount is: 0.0 ;m1_m4_m2_m3:ClC=1C(C(=C(C(C1Cl)=O)C#N)C#N)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=CC=2C(CCCC2C1)=O)CCCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-[3-(3-benzyloxy-5,6,7,8-tetrahydro-2-naphthyl) propyl]benzoic acid (1.6 g) in ethyl acetate (50 ml) was added water (1 ml) and 2,3-dichloro-5,6-dicyanobenzoquinone (1.9 g). The mixture was stirred for 2 hours, the solvent evaporated and the residue subjected to chromatography on silica gel, eluting with 0.1% formic acid in EtOAc. The residue was purified by trituration with diethyl ether to give the title compound (0.3 g) mpt. 155°-160° C. |
Here is a chemical reaction formula: Reactants are m3_m4:OC=1C=C(C=CC1)NC(C)=O, amount is: 0.0 MOLE;m1:C(C=C)OC=1C=C(C=CC1)NC(C)=O, amount is: 0.0 ;m2:C(C=C)OC=1C=C(CCl)C=CC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4:O(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m5:CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)C1=C(C=C(C=C1)NC(C)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(3-allyloxyphenyl)acetamide (13.2 g) prepared by a similar method to that of Example 2, Footnote c (A), from N-(3-hydroxyphenyl)acetamide, in Ph2O (100 ml) was heated at 250° C. for 10 minutes, cooled and diluted with hexane (100 ml) to give crystals. The crystals were re-crystallised from ethyl acetate. The liquors were evaporated and dissolved in 0.2M aqueous NaOH, filtered though Celite, and acidified with 1M aqueous HCl solution to give N-(4-allyl-3- hydroxyphenyl)acetamide (3.6 g) mpt. 164°-165° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)OC1=C(C=CC(=C1)NS(=O)(=O)C1=CC=CC=C1)CCCC1=CC=C(C(=O)OCC)C=C1, amount is: 0.0 MOLE;m0_m1_m2:C(C=C)OC=1C=C(CCl)C=CC1, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC(=C1)NS(=O)(=O)C1=CC=CC=C1)CCCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The title compound was prepared from ethyl 4-[3-(2-benzyloxy-4-benzenesulphonamidophenyl)propyl]benzoate by a similar method to that of Example 1, (A). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m4_m3:[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)N, amount is: 0.0 ;m1_m2_m4_m3:Cl.CN(CCCN=C=NCC)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CCOC(=O)C, amount is: 0.0 MOLE,Catalysts are m1_m2_m4_m3:CN(C)C=1C=CN=CC1, amount is: 0.0 .Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)NC(C1=CC=C(C=C1)CCCC1=C(C=CC=C1)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-[3-(2-benzyloxyphenyl)propyl)benzoic acid 0.2 g), 4-nitrobenzenesulphonamide (0.12 g), DMAP (0.15 g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.12 g) was stirred for 65 hours. The mixture was diluted with EtOAc, washed with water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate, to give the title compound (0.21 g) mpt. 112°-113° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)SC)CCCC1=CC=C(C=C1)C(=O)NCCO, amount is: 0.0 ;m1_m3_m2_m4:I(=O)(=O)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CO, amount is: 0.0 ;m1_m3_m2_m4:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)S(=O)C)CCCC1=CC=C(C=C1)C(=O)NCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A slurry of 4-[3-(2-benzyloxy-5-methylthiophenyl)-propyl]-N-(2-hydroxyethyl)benzenecarboxamide (0.22 g) in methanol (10 ml) was added to a stirred solution of sodium metaperiodate (0.113 g) in water (1 ml) maintained at 0° C. by external cooling. The reaction mixture was stirred at 0° C. for 2 hours, then concentrated to a volume of approximately 2 ml. This residue was dissolved in ethyl acetate (10 ml), the ethyl acetate solution was dried (anhydrous magnesium sulphate) and the solution evaporated to dryness. The residue was subjected to chromatography on silica (Merck) eluted with a mixture of methanol/ethyl acetate (1:9 v/v). The only porduct obtained was triturated with ethyl acetate (2 ml) to give 4-[3-(2-benzyloxy-5-methylsulphinylphenyl)propyl]-N-(2-hydroxyethyl)-benzenecarboxamide (mp. 105°-108° C.; 43% yield). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C)(=O)C=1C=CC(=C(C1)CCCC1=CC=C(C=C1)C(=O)NCCO)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:C(C)(=O)C=1C=CC(=C(C1)CCCC1=CC=C(C=C1)C(=O)NCCO)OCC1=CC=CC=C1, amount is: 0.0 MOLE;m1_m2_m3_m4:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(C)=NO)CCCC1=CC=C(C=C1)C(=O)NCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-[3-(5-acetyl-2-benzyloxyphenyl)propyl]-N-(2-hydroxyethyl)benzenecarboxamide (0.5 g) (example 2, compound 45) hydroxylamine hydrochloride (0.16 g) in pyridine (5 ml) was heated at 60° C. for 2 hours. The pyridine was removed and the residue subjected to flash chromatography on silica, eluting with a mixture of ethyl acetate/hexane (4:1 v/v) to yield in the appropriate fractions, 4-[3-(2-benzyloxy-5-(1-hydroxyiminoethyl)phenyl)propyl]-N-(2-hydroxyethyl)benzenecarboxamide (m.p. 131°-2° C.; yield 56%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C=CC1=CC=C(C=C1)C(=O)Cl, amount is: 0.0 ;m1_m3_m2_m4:NCCO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:ClCCl, amount is: 0.0 ;m1_m3_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)/C=C/C1=CC=C(C=C1)C(=O)NCCO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-[2-(2-benzyloxyphenyl)ethenyl]-benzenecarbonyl chloride (0.98 g) in dichloromethane (5 ml) was added dropwise to a solution of 2-aminoethanol (0.51 ml) in dichloromethane (15 ml) maintained at 0° C. The reaction mixture was allowed to warm to ambient temperature and was stirred for 16 hours. The reaction mixture was washed with water (20 ml) and saturated aqueous sodium bicarbonate (20 ml) and dried. Evaporation of the solvent left a solid residue which was crystallised twice from methanol to give (E)-4-[2-(2-benzyloxyphenyl)ethenyl]-N-(2-hydroxyethyl)benzenecarboxamide (m.p. 149°-151° C.; yield 19%) containing about 4% of the related Z-isomer. |
Here is a chemical reaction formula: Reactants are m5:C(C)N(CC)CC, amount is: 0.0 ;m4_m7:Cl.C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=C(C=C1)N, amount is: 0.0 ;m1_m2_m3_m6:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-], amount is: 0.0 ;m1_m2_m3_m6:N1=C(C=CC=C1)CC(=O)O, amount is: 0.0 ;m1_m2_m3_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:CN(C=O)C, amount is: 0.0 ;m1_m2_m3_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=C(C=C1)NC(=O)CC1=NC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Diphenylphosphoryl azide (0.46 ml) was added dropwise to a stirred suspension of 2-pyridylacetic acid (0.367 g) and triethylamine (0.3 ml) in N,N-dimethylformamide (10 ml) maintained at 0° C. A suspension of 4-[3-(2-benzyloxyphenyl)propyl]benzeneamine hydrochloride (0.75 g) in N,N-dimethylformamide (10 ml) containing triethylamine (0.9 ml) was added rapidly to the reaction mixture. Stirring was continued at ambient temperature for 16 hours and the reaction mixture was concentrated to small volume. The residue was partitioned between water and diethyl ether. The diethyl ether extract was washed once each with saturated aqueous sodium bicarbonate (20 ml) and brine (20 ml) and dried. The gum obtained on removal of the solvent was subjected to chromatography on silica (Merck 9385) eluted with a mixture of ethyl acetate and hexane (1:1 v/v). The gum obtained was triturated with ether at 0° C. to give 4-[3-(2-benzyloxy-phenyl)propyl]-N-(2-pyridylmethylcarbonyl)benzeneamine (m.p. 61°-2° C.; yield 0.63 g 68%). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=C(C=C1)C(=O)O, amount is: 0.0 ;m1_m2_m3_m4:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-], amount is: 0.0 ;m1_m2_m3_m4:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m3_m4:C(C)(C)(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)C1=C(C=CC(=C1)CCCC1=C(C=CC=C1)OCC1=CC=CC=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-[3-(2-benzyloxyphenyl)propyl]benzene carboxylic acid (8.39 g), diphenylphosphoryl azide (5.74 ml) and triethylamine (7.1 ml) in t-butanol (80 ml) was heated under reflux in an argon atmosphere for 16 hours. The reaction mixture was evaporated to dryness and the residue partitoned between ethyl acetate and water. The ethyl acetate extract was washed once each with 2N HCl, water, saturated aqueous sodium bicarbonate solution and brine (20 ml each time) and dried (MgSO4). The solvent was evaporated and the residue subjected to flash chromatography eluted with a mixture of dichloromethane:hexane (1:1 v/v) to give N t-butyloxycarbonyl-4-{3-(2-benzyloxyphenyl)propyl]benzene-amine 7.69 g m.p. 86°-8° C. which was used directly in the next step. |
Here is a chemical reaction formula: Reactants are m1_m2:N1=CC(=CC=C1)CCNC(C1=CC=C(C=C1)CCCC1=C(C=CC=C1)OCC1=CC=CC=C1)=O, amount is: 0.0 ;m1_m2:C(C)I, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[I-].C(C)[N+]1=CC(=CC=C1)CCNCC1=CC=C(C=C1)CCCC1=C(C=CC=C1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(2-(3-pyridyl)ethyl)-4-[3-(2-benzyloxyphenyl) propyl]benzamide(1 g) and ethyl iodide (0.54 g) was stirred in DMF (5 ml) at 100° C. for 4 hours. The solvent was evaporated and the residue crystallised from ethyl acetate to give 1-ethyl-3-[2-(4-[3-(2-benzyloxyphenyl)propyl]benzylamino)ethyl]pyridinium iodide (463 mg); mpt 89° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m3_m5:CCN(CC)CC, amount is: 0.0 ;m1_m2_m3_m5:C=1C=CC(=CC1)P(=O)(C=2C=CC=CC2)N=[N+]=[N-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m0_m4:O1CCOCC1, amount is: 0.0 MOLE;m1_m2_m3_m5:O1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N-]=C=O.C(C1=CC=CC=C1)OC1=C(C=CC=C1)CCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The solution of 4-[3-(2-benzyloxyphenyl)propyl]benzene isocyanate in dioxane was prepared by heating a mixture of 4-[3-(2-benzyloxyphenyl)propyl]benzoic acid (2.0 g), Et3N (1.61 ml) and DPPA (1.31 ml) in dioxane (20 ml) for 3 hours. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC1=C(C=O)C=CC=C1, amount is: 0.0 ;m1_m2_m3:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CO)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-benzyloxybenzaldehyde (5 g, Apin) and sodium borohydride (1.4 g) in ethanol (50 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl alcohol (4.91 g) as an oil. |
Here is a chemical reaction formula: Reactants are m2:P(Br)(Br)Br, amount is: 0.0 ;m1_m3:C(C1=CC=CC=C1)OC1=C(CO)C=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)OCC, amount is: 0.0 ;m4:C(C)OCC, amount is: 0.0 ;m1_m3:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CBr)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-benzyloxybenzyl alcohol (4.83 g) in diethyl ether (40 ml) was added dropwise, at 0° C., a solution of phosphorus tribromide (6.27 g) in diethyl ether (10 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (100 ml) and filtered through a pad of silica gel washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxybenzyl bromide (5.88 g) as an oil. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)Br, amount is: 0.0 MOLE;m1:OC1=C(C=CC=C1)C(C(=O)O)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(C(=O)OCC1=CC=CC=C1)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-(2-Hydroxyphenyl)propionic acid was benzylated with two equivalents of benzyl bromide using the process described in Example 85, footnote a to give benzyl 2-(2-benzyloxyphenyl)propionate. |
Here is a chemical reaction formula: Reactants are m2:Cl.CN, amount is: 0.0 MOLE;m1:C(C1=CC=CC=C1)OC1=C(C=CC=C1)C(C(=N)N)C, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:CNC(C(C)C1=C(C=CC=C1)OCC1=CC=CC=C1)=N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: N-Methyl-2-(2-benzyloxyphenyl)propionamidine was prepared by the method described in Example 88 for the synthesis of 2-(2-benzyloxy-phenyl) propionamidine using methylamine hydrochloride instead of ammonium hydrochloride. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:CN1C(=NC=C(C1=O)C(=O)OCC)CCC1=C(C=CC=C1)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CN1C(=NC=C(C1=O)C(=O)OC)CCC1=C(C=CC=C1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of ethyl N1-methyl-2-[2-(2-benzyloxyphenyl)-ethyl]pyrimidin-6(1 H)-one-5-carboxylate (0.5 g) and para-toluene sulphonic acid (30 mg) in methanol was heated under reflux for 18 hours, 150 mg of para-toluene sulphonic acid was added and the mixture heated under reflux for a further 24 hours. The solvent was evaporated to give methyl N1-methyl-2-[2-(2-benzyloxyphenyl)ethyl]-pyrimidin-6(1 H)-one-5-carboxylate (410 mg). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:BrC1=CC=C(C(C=O)=C1)O, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(C=O)C=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-bromosalicylaldehyde (12 g), potassium carbonate (16.5 g) and benzyl bromide (7.8 ml) in DMF (50 ml) was stirred for 18 hours, poured into ethyl acetate (100 ml), washed with 0.05M HCl (100 ml), sodium bicarbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated. The residue was triturated with hexane/diethyl ether to give 2-benzyloxy-5-bromo-benzaldehyde (15.8 g) mp.70°-72° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC1=C(C=O)C=C(C=C1)Br, amount is: 0.0 ;m1_m2_m3:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CO)C=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-benzyloxy-5-bromobenzaldehyde (14.55 g) and sodium borohydride (2.6 g) in ethanol (250 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl alcohol (14.85 g) as an oil. To a solution of 2-benzyloxy-5-bromobenzyl alcohol (14.75 g) in diethyl ether (150 ml) was added dropwise, at 0° C., to a solution of phosphorus tribromide (13.68 g) in diethyl ether (40 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (200 ml) and filtered through a pad of silica gel (200 g) washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl bromide (15.2 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(C1=CC=CC=C1)OC1=C(CO)C=C(C=C1)Br, amount is: 0.0 ;m1_m3_m2_m4:P(Br)(Br)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)OCC, amount is: 0.0 ;m1_m3_m2_m4:C(C)OCC, amount is: 0.0 ;m1_m3_m2_m4:C(C)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CBr)C=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-benzyloxy-5-bromobenzaldehyde (14.55 g) and sodium borohydride (2.6 g) in ethanol (250 ml) was stirred under argon for 1 hour. The solvent was evaporated, the residue dissolved in ethyl acetate and added dropwise to 0.1M hydrochloric acid solution (200 ml) at 0° C. The organic solution was washed with saturated aqueous sodium hydrogen carbonate (100 ml) and brine (100 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl alcohol (14.85 g) as an oil. To a solution of 2-benzyloxy-5-bromobenzyl alcohol (14.75 g) in diethyl ether (150 ml) was added dropwise, at 0° C., to a solution of phosphorus tribromide (13.68 g) in diethyl ether (40 ml). The mixture was warmed to ambient temperature, diluted with diethyl ether (200 ml) and filtered through a pad of silica gel (200 g) washing with 1 litre of diethyl ether. The combined organic solution was washed with saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml), dried (sodium sulphate), filtered and evaporated to give 2-benzyloxy-5-bromobenzyl bromide (15.2 g). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC1=C(CCC2=CC=C(C(=N2)Cl)C(=O)OC)C=C(C=C1)Br, amount is: 0.0 ;m1_m2_m3:C[O-].[Na+], amount is: 2.5 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CCC2=CC=C(C(=N2)OC)C(=O)OC)C=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of methyl 6-[2-benzyloxy-5-bromophenethyl]-2-chloro-3-pyridinecarboxylate (7.0 g) and sodium methoxide (2.5 mole equivalents) in methanol was heated at 140° C. for 5 hours in a Carius Tube. The solvent was evaporated and the residue extracted with ethyl acetate and washed with saturated aqueous NH4Cl, water and brine. The organic solution was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on 7734 silica gel, eluting with 1% MeOH/CH2Cl2, to give methyl 6-[2-benzyloxy-5-bromophenethyl]-2-methoxy-3-pyridinecarboxylate (6.16 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC1=C(CCC2=CC=C(C(=N2)Cl)C(=O)OC)C=C(C=C1)Br, amount is: 0.0 ;m1_m3_m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=C(CCC2=CC=C(C(=N2)Cl)C(=O)N)C=C(C=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of methyl 6-[2-benzyloxy-5-bromophenethyl]-2-chloro-3-pyridinecarboxylate (2.0 g) in ethanol (60 ml) saturated with ammonia was heated at 177° C. under pressure for 6 hours. The solvent was evaporated and the residue subjected to chromatography on silica gel (7734). Two products were isolated. The first was eluted with 2.5% ethyl acetate/CH2Cl2 and the second with 5% MeOH/CH2Cl2. The first product was identified as a mixture of the methyl and ethyl esters of 6-[2-benzyloxy-5-bromophenethyl]-2-amino-3-pyridinecarboxylic aicd (0.3 g). The second produce was identified as the title compound (0.6 g) mpt. 142°-144° C. |
Here is a chemical reaction formula: Reactants are m4:CCOC(=O)/N=N/C(=O)OCC, amount is: 0.0 ;m1_m5:OC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m2_m3:OCC=1C=NC=CC1, amount is: 0.0 ;m2_m3:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=CC(=CC=C1)COC1=C(C=CC=C1)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(2-hydroxyphenyl)propyl]benzoate (1.35 g, 5 mmol) was dissolved in 0.2 ml of THF. The solution was treated with 3-hydroxymethylpyridine (0.6 g, 5.5 mmol) and triphenylphosphine (1.44 g, 5.5 mmol). To this mixture was added slowly diethylazodicarboxylate (0.96 g, 5.5 mmol). The reaction mixture was stired for 72 hours and the solvent was evaporated. The amide residue was purified by chromatography (methanol, dichloromethane) to give methyl 4-[3-(2-(3-pyridylmethyloxy)phenyl)propyl]benzoate as a pink oil (1.03 g, 57%) MS (CI+):362 [M+H]+. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C1=CC=CC=C1)OC1=NC=NC=C1CCCC1=CC=C(C(=O)OC(C)(C)C)C=C1, amount is: 0.0 ;m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=NC=NC=C1CCCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: tert-Butyl 4-[3-(4-(benzyloxy)pyrimid-5-yl)propyl]benzoate (0.36 g, 0.92 mmol) was dissolved in dichloromethane (0.7 ml) and treated with trifluoro-acetic acid (1.05 g, 9.2 mmol). The reaction was stirred at amibent temperature for 2 hours. The mixture was partitioned between EtOAc/water and the aqueous layer extracted with EtOAc. The organic layers were combined, dried (MgSO4) and evaporated and the solid was triturated with hexane and recrystallised from isopropanol/water. The cream coloured solid was taken up in THF, filtered through Celite and evaporated to give the title product. |
Here is a chemical reaction formula: Reactants are m1_m2:N1=CNC(C(=C1)C#CC1=CC=C(C(=O)OC(C)(C)C)C=C1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CCOC(=O)C, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 MOLE.Products are 0:N1=CNC(C(=C1)CCC1=CC=C(C(=O)OC(C)(C)C)C=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Tert-butyl 4-[2-(pyrimidin-4(3 H)-one-5-yl)ethynyl]benzoate (0.59 g, 2.0 mmol) was dissolved in EtOAc (20 ml) and treated with palladium-on-carbon (0.30 g, 10%]. The reaction was placed under a hydrogen atmosphere and stirred overnight at ambient temperature. The reaction was filtered and evaporated to give tert-butyl 4-[2-(pyrimidin-4(3 H)-on-5-yl)ethyl]benzoate which was used without further purification (0.6 g, quantitative). |
Here is a chemical reaction formula: Reactants are m1_m3:N1=CNC(C(=C1)CCC1=CC=C(C(=O)OC(C)(C)C)C=C1)=O, amount is: 0.0 ;m2:P(=O)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:CN(C1=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=NC=NC=C1CCC1=CC=C(C(=O)OC(C)(C)C)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: tert-Butyl 4-[2-(pyrimidin-4(3 H)-on-5-yl)ethyl]benzoate (0.6 g,) was dissolved in N,N-dimethylaniline (5 ml) and treated with phosphorous-oxy-chloride (1.53 g 10 mmol). The reaction was heated to 100° C. for 2.5 hours and then evaporated at reduced pressure. The residue was diluted with EtOAc, washed (1N HCl 2×, H2O, saturated brine), dried over MgSO4 and evaporated to give tert-butyl 4-[2-(4-chloropyrimidin-5-yl)ethyl]benzoate as a brown oil (0.5 g, 64%) which was used without further purification. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[Na+], amount is: 0.0 ;m1_m3:C(C1=CC=CC=C1)OC1=NC=CC=C1CCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=NC=CC=C1CCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(2-benzyloxypyrid-3-yl)ethyl]benzoate was dissolved in EtOH (5 ml) and treated with NaOH (1N, 1.04 ml). The reaction was stirred at ambient temperature for 48 hours, 1N HCL (1.04 ml) was added and the precipitate was filtered and recrystllised from iso-propanol to give 4-[2-(2-benzyloxypyrid-3-yl)ethyl]benzoic acid as a white solid (0.054 g, 38%). |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)O, amount is: 0.0 ;m3_m7:ClC1=C(C#N)C=CC=N1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7:C1CCOC1, amount is: 0.0 ;m1_m5:CCCCCC, amount is: 0.0 MOLE;m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=NC=CC=C1C#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Sodium hydride (60%, 2.89 g, 72.3 mmol) was washed with hexane (1×) and suspended in THF (50 ml). Anhydrous benzyl alcohol (8.57 g, 79.3 mmol) was added dropwise and the reaction mixture was stirred for 30 minutes. A solution of 2-chloronicotinonitrile (10.0 g, 72.2 mmol) in THF (50 ml) was added via a syringe (exotherm). The reaction was stirred at ambient temperature for 18 hours then water was added to quench the reaction. The reaction mixture was partitioned between EtOAc/water and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2, CH2Cl2) to give 2-benzyloxy-3-cyanopyridine as a pale yellow oil which crystallised on standing (11.4 g, 75%). |
Here is a chemical reaction formula: Reactants are m3_m5:C(C1=CC=CC=C1)OC1=NC=CC=C1C=O, amount is: 0.0 ;m2:C[Si](C)(C)[N-][Si](C)(C)C.[Li+], amount is: 0.0 ;m1:[Br-].COC(=O)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ;m3_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=NC=CC=C1C=CC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4-Methoxycarbonylbenzyl)triphenylphosphonium bromide (16.6 g, 33.8 mmol) was suspended in THF (70 ml) under Argon. Lithium bis(trimethylsilyl)amide (1M in THF, 40.5 ml) was added. The reaction mixture was stirred for 1 hour at ambient temperature; the colour changed to orange. 2-Benzyloxy-3-pyridinecarbaldehyde (7.2 g, 33.8 mmol) was added as a solution in THF (50 ml) and the reaction mixture was stirred at amibent temperature overnight (shielded from light). The reaction mixture was partitioned between EtOAc/water, the organic phase was dried (MgSO4) and evaporated. Purification by chromatography (SiO2, eluting with CH2Cl2 /hexane) gave methyl 4-[2-(2-benzyloxy-3-pyridyl)ethenyl]benzoate (9.2 g, 79%). |
Here is a chemical reaction formula: Reactants are m2:[H][H], amount is: 0.0 MOLE;m1_m4:C(C1=CC=CC=C1)OC1=NC=CC=C1C=CC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3:C(C)O, amount is: 0.0 ;m1_m4:C(C)O, amount is: 0.0 ,Catalysts are m5_m3:[Rh], amount is: 0.0 .Products are 0:C(C1=CC=CC=C1)OC1=NC=CC=C1CCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of rhodium on alumina (5%, 0.1 g) in ethanol (20 ml) was flushed well with argon. A solution of the methyl 4-[2-(2-benzyloxypyrid-3-yl)ethenyl]benzoate (1.0 g, 2.9 mmol) in ethanol (60 ml) was added. The reaction was transferred to a manometer under an atmosphere of hydrogen and the reaction was stirred at ambient temperature until 1.4 equivalents hydrogen had been taken up. The reaction mixture was filtered and evaporated and the residue subjected to chromatography on SiO2 (CH2Cl2 /hexane) to give 4-[2-(2-benzyloxypyrid-3-yl)ethyl]benzoic acid (0.5 g, 49%). |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m4_m2:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m4_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.1 g, 0.3 mmol) in EtOH (1 ml) was treated with aqueous NaOH solution (0.6 ml 1N). The reaction was stirred at ambient temperature for 18 hours and then treated with HCl soltuion (0.6 ml, 1N). The resulting precipitate was filtered and recrystallised from isopropanol to give the title product. |
Here is a chemical reaction formula: Reactants are m2_m5:[OH-].[K+], amount is: 0.0 MOLE;m3:C(C1=CC=CC=C1)Br, amount is: 0.0 MOLE;m1_m4:Cl.OC=1C(=NC=CC1)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(C)O, amount is: 0.0 ;m1_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a suspension of 3-hydroxy-2-hydroxymethylpyridine hydrochloride (7.0 g, 12.4 mmol) in ethanol (37.5 ml) was added a solution of KOH pellets (85% 1.6 g, 24.7 mmol) in ethanol (25 ml). The reaction was stirred for 5 minutes at ambient temperature and then benzyl bromide was added (2.11 g, 12.36 mmol). The reaction mixture was stirred at ambient temperature for 48 hours, filtered and evaporated. The residue was purified by chromatography (EtOAc, CH2Cl2) to give 3-benzyloxy-2-hydroxymethylpyridine as a colourless solid (1.55 g, 58%) [J. Med. Chem., 15, (1972) 615] m.p. 78.7°-79.2° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)(Cl)Cl, amount is: 0.0 ,Catalysts are m1_m2_m3:[O-2].[O-2].[Mn+4], amount is: 0.0 .Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-benzyloxy-2-hydroxymethylpyridine (0.25 g, 1.16 mmol) in chloroform (15 ml) was treated with manganese dioxide (0.45 g, 6.34 mmol). The reaction mixture was heated to reflux and held at reflux for 18 hours. The reaction mixture was then filtered through Celite and evaporated to give a yellow gum. This gum was purified by chromatography (EtOAc/CH2Cl2) to give 3-benzyloxy-2-pyridinecarbaldehyde as a colourless gum (0.15 g, 62%). |
Here is a chemical reaction formula: Reactants are m2:C[Si](C)(C)[N-][Si](C)(C)C.[Li+], amount is: 0.0 ;m3_m5:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=O, amount is: 0.0 ;m1:[Br-].COC(=O)C1=CC=C(C[P+](C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 ;m3_m5:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4-Methoxycarbonylbenzyl)triphenylphosphonium bromide (4.42 g, 9.00 mmol) was suspended in THF (50 ml) under argon. Lithium bis-(trimethylsilyl)amide (1M in THF, 10.8 ml) was added and the deep orange reaction was stirred at ambient temperature for 1 hour. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (2.0 g, 9.4 mmol) in THF (20 ml) was added and the reaction was stirred at ambient temperature for 2 hours 30 minutes. The reaction was partitioned between EtOAc/water, the aqueous phase was extracted with EtOAc, the organic layers were combined, dried (MgSO4) and evaporated. The residue was purified by chromatography (EtOAc/CH2Cl2) to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate as a yellow oil. (3.01 g) . |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CCO, amount is: 0.0 ;m1_m2:CCOC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC=1C(=NC=CC1)CCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethenyl]benzoate (2.0 g, 5.8 nnol) was partially dissolved in EtOAc (20 ml) and EtOH (10 ml). The reaction vessel was flushed with argon, palladium-on-carbon (0.2 g, 10%) was added and the reaction was flushed with argon followed by hydrogen. The reaction was stirred at ambient temperature for 18 hours, filtered and evaporated to give methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate as a pale orange solid (1.3 g, 90%) which was used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:OC=1C(=NC=CC1)CCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m4_m2_m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m4_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of methyl 4-[2-(3-hydroxy-2-pyridyl)ethyl]benzoate (1.1 g, 4.3 mmol) in DMF (30 ml) was treated with benzyl bromide (0.89 g, 5.2 mmol) and potassium carbonate (0.72 g, 5.2 mmol). The reaction was stirred at ambient temperature overnight and then, partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2) eluting with CH2Cl2 /EtOAc to give methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.94 g, 53%) as a low melting yellow solid. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m1_m3:C(O)CN, amount is: 0.0 ;m2:O, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:OCCNC(C1=CC=C(C=C1)CCC1=NC=CC=C1OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[2-(3-benzyloxy-2-pyridyl)ethyl]benzoate (0.20 g, 0.576 mmol) was dissolved in ethanolamine (3 ml) and heated to 160° C. under argon for 2 hours. Water was added (3 ml) and the aqueous layers were extracted with ethyl acetate and the organic phase was dried (MgSO4) and evaporated. The residue was recrystallised from EtOAc/hexane and washed with ether to give the title product (0.064 g, 29%). |
Here is a chemical reaction formula: Reactants are m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5:C(C1=CC=CC=C1)OC1=NC=CC=C1CCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m5:NCC1=NC=CC=C1, amount is: 0.0 ;m4:C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)N=[N+]=[N-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=C(C=CC=C1)CNC(C1=CC=C(C=C1)CCC=1C(=NC=CC1)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-[2-(2-benzyloxy-3-pyridyl)ethyl]benzoic acid (0.48 g, 1.44 mmol) and 2-aminomethylpyridine (0.189 g, 1.748 mmol) were dissolved in DMF (20 ml) and cooled to 0° C. Triethylamine (0.15 g, 1.5 mmol) was added followed by diphenylphosphorylazide (0.41 g, 1.48 mmol). The reaction mixture was stirred under argon and allowed to warm to ambient temperature overnight. The reaction was partitioned between EtOAc/water, the organic phase was washed with aqueous sodium bicarbonate, water, dried (MgSO4) and evaporated. The residue was purified by flash chromatography (MeOH/CH2Cl2) followed by recrystallisation from EtOAc/hexane and then from EtOH/water to give the title product. |
Here is a chemical reaction formula: Reactants are m1:[Br-].C(=O)(O)C1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m2_m4:C(C1=CC=CC=C1)OC1=NC=CC=C1C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C1CCOC1, amount is: 0.0 ;m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC1=NC=CC=C1C=CCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (10.9 g, 22.2 mmol) was suspended in THF (80 ml) and the flask was flushed with argon. Lithium bis(trimethylsilyl)amide (1M in THF, 48.8 ml) was added dropwise and the reaction stirred for 1 hour, becoming dark brown. A solution of 2-benzyloxy-3-pyridinecarbaldehyde (4.73 g, 22.2 mmol) in THF (20 ml) was added slowly. The reaction was stirred at ambient temperature for 18 hours (shielding from light alumimium foil). The reaction mixture was then partitioned between Et2O/water, the organic layer was washed with water and the aqueous layers were combined, acidified with HCl and extracted with EtOAc. The organic phase was dried (MgSO4) and evaporated and purified by colum chromtagraphy with MeOH/CH2Cl2 to give the title product. |
Here is a chemical reaction formula: Reactants are m2_m5:C[Si](C)(C)[N-][Si](C)(C)C.[Li+], amount is: 0.0 MOLE;m1:[Br-].C(=O)(O)C1=CC=C(C=C1)CC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m3_m6:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C1CCOC1, amount is: 0.0 MOLE;m4:C1CCOC1, amount is: 0.0 ;m3_m6:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (2-(4-Carboxyphenyl)ethyl)triphenylphosphonium bromide (0.58 g, 1.17 mmol) was suspended in THF (7 ml) and lithium bis(trimethylsilyl)amide was added (1M in THF, 2.46 ml). The reaction mixture turned orange and was allowed to stir for 1 hour at ambient temperature. A solution of 3-benzyloxy-2-pyridinecarbaldehyde (0.25 g, 1.17 mmol) in THF (3.5 ml) was added slowly. The reaction was stirred at ambient temperature for 1 hour. The reaction was quenched by the addition of water (8 ml) and ether (8 ml). The layers were separated, the ether layer was washed with water and the as aqueous layers were combined, acidified with 1N HCl and extracted with EtOAc (2×). The organic extracts were dried (MgSO4) and evaporated to give the title product as a mixture of isomers (2.7 g 66%). |
Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 ;m1_m4:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CCO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCCC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl)benzoate (0.3 g, 0.83 mmol) was dissolved in EtOH (3 ml) and treated with 1N NaOH (1.66 ml). The reaction was stirred at ambient temperature for 18 hours. A solution of hydrochloric acid (1N, 1.66 ml) was added and the resulting precipitate was filted and recrystallised from ethanol to give the title product as a white solid (0.054 g). |
Here is a chemical reaction formula: Reactants are m1_m3:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CCC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m3:CO, amount is: 0.0 ;m2:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-[3-(3-Benzyloxy-2-pyridyl)prop-2-enyl)benzoic acid (0.1 g, 0.29 mmol) was dissolved in methanol (5 ml) and cooled to 0° C. To the solution was added thionyl chloride (0.086 g, 0.73 mmol). The reaction was allowed to warm to ambient temperature and stirred at ambient temperature for 18 hours. The reaction mixture was then evaporated, the residue partitioned between ethyl acetate and water and the organic phase dried (MgSO4) and evaporated. The residue was purified by chromatography (SiO2 EtOAc/CH2Cl2) to give methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate as an oil (0.05 g, 49%). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C1=CC=CC=C1)OC=1C(=NC=CC1)C=CCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:C(C)O, amount is: 0.0 ;m3_m4:CCOC(=O)C, amount is: 0.0 ,Catalysts are m3_m4:[Pd], amount is: 0.0 .Products are 0:OC=1C(=NC=CC1)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(3-benzyloxy-2-pyridyl)prop-2-enyl]benzoate (1.5 g, 4.2 mmol) was dissolved in ethanol (5 ml) and EtOAc (15 ml), treated with 10% palladium on carbon (0.15 g) and placed under a hydrogen atmosphere. The mixture was stirred at ambient temperature for 10 hours and filtered and evaporated to give methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate as a yellow oil (0.88 g, 77%). |
Here is a chemical reaction formula: Reactants are m4:[K], amount is: 0.0 MOLE;m1_m5:OC=1C(=NC=CC1)CCCC1=CC=C(C(=O)OC)C=C1, amount is: 0.0 ;m2_m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC=1C(=NC=CC1)CCCC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl 4-[3-(3-hydroxy-2-pyridyl)propyl]benzoate (0.87 g, 3.2 mmol) was dissolved in DMF (5 ml) and treated with benzyl bromide (0.66 g, 3.9 mmol) and potassium carbonate (0.53 g, 3.8 mmol). The reaction was stirred at ambient temperature potassium overnight and then partitioned between EtOAc/water. The organic phase was washed well with water, dried (MgSO4) and evaporated. The residue was purified (SiO2, CH2Cl2 /EtOAc) to give methyl 4-[3-(3-benzyloxy-2-pyridyl)propyl]benzoate as a pale yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m2:P(CC)CC, amount is: 0.0 ;m1_m2:N(=NC(C#N)(C)C)C(C#N)(C)C, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(CC)P(CCP(CC)CC)CCP(CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of n-PrP(CH=CH2)2 (1.29 g, 10.0 mmol), Et2PH (2.25 g, 25.0 mmol) and 2,2'-azobis(isobutyronitrile) (AIBN, 30 mg) in a closed flask under inert atmosphere was irradiated by a GE Sunlamp (275 W) one foot away for 24 hours. The resulting colorless liquid was stripped of volatiles under vacuum and vacuum distilled to give 3.1 g (97% yield) of product collected at 132°-135° C./0.35 mm Hg. 31P-NMR (toluene): δ--18.5 (2P); δ--22.8 (1P). |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m6:[Cl-].[Zn+2].[Cl-], amount is: 0.0 ;m1_m5_m2_m6:[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[Co], amount is: 0.0 ;m3_m4:[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[Co], amount is: 0.0 MOLE;m3_m4:[Cl-].[Zn+2].[Cl-], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m6:O, amount is: 0.0 ;m1_m5_m2_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[Co+3].[Co+3].[Zn+2].[Zn+2].[Zn+2], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of zinc chloride (26.65 g; 0.1956 mole) in water (26.65 g) was added rapidly to an agitated solution of potassium hexacyanocobaltate (13.00 g, 0.0391 mole) in water (263.35 g). The potassium hexacyanocobaltate solution was maintained at 40° C. during addition of the zinc chloride solution. A colorless precipate of zinc hexacyanocobaltate particles formed immediately upon addition. After stirring for 15 minutes at 40° C., dimethoxyethane (84.00 g; 0.9321 mole) was added to the aqueous catalyst slurry. The resulting mixture was stirred for an additional 30 minutes and the zinc hexacyanocobaltate zinc chloride dimethoxyethane water complex catalyst recovered by filtration using a horizontal basket centrifugal filter and a light weight nylon fabric filter medium. After washing with 300 mL dimethoxyethane and drying in air at ambient temperature and pressure, the filter cake obtained was quite soft and could be easily crushed to a fine powder. |
Here is a chemical reaction formula: Reactants are m1_m2:Br, amount is: 0.0 ;m1_m2:C(C)(=O)O[C@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H](O1)COC(C)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.C(C)(=O)O.Br[C@@]1(O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Hydrobromic acid (30% in acetic acid, 11.85 ml, 55.4 mmol) was added to β-D-glucose pentaacetate (12.01 g, 30.8 mmol) at 0° C. After 10 minutes, the resulting solution was warmed to room temperature and stirred for 4 hours. The reaction mixture was slowly poured, with stirring, into ice water (250 ml) and was stirred until the product solidified. The product was collected by vacuum filtration and washed with cold water. The white solid was dissolved in carbon tetrachloride (60 ml) and washed with H2O (1×20 ml), saturated aqueous NaHCO3 (3×20 ml, until pH=7), H2O (1×20 ml), dried with CaCl2, and poured into cold petroleum ether (250 ml). After 30 min, the crystalline product was collected by vacuum filtration to give the target compound as a white solid (10.0 g, 80%). |
Here is a chemical reaction formula: Reactants are m3:C(C)(C)(C)[Si](C1=CC=CC=C1)(C1=CC=CC=C1)Cl, amount is: 0.0 ;m1_m4_m2:O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C, amount is: 0.0 ;m1_m4_m2:N1C=NC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](OC)O1)O)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of methyl β-D-glucopyranoside (5 g, 25.7 mmol) in 51 mL of dry DMF was added at room temperature imidazole (5.46 g, 80.2 mmol) followed by tert-butyldiphenyl-silyl chloride (11.3 mL, 43.4 mmol). The solution was heated to 50° C. for 24 hours and the DMF was removed under reduced pressure. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with H2O (1×100 mL), saturated aqueous NaCl (1×100 mL), and dried over magnesium sulfate. Concentration and flash chromatography (silica, 4% methanol in dichloromethane) provided pure target compound (9.82 g, 88%) as a white foam. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:[Si](C1=CC=CC=C1)(C1=CC=CC=C1)(C(C)(C)C)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](OC)O1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1CCOC1, amount is: 0.0 ;m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)O[C@H]1[C@H](OC)O[C@@H]([C@H]([C@@H]1OCC1=CC=CC=C1)OCC1=CC=CC=C1)CO, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (2.81 g, 3.98 mmol) in dry THF (40 ml, 0.1M) at room temperature was added tetrabutyl ammonium fluoride (4.37 ml, 4.37 mmol, 1M solution in THF). After stirring for 3 hours, the reaction solution was diluted with ethyl acetate (300 ml) and washed with water (1×100 ml) and saturated aqueous NaCl (1×100 ml), and dried with magnesium sulfate. Concentration and flash chromatography (silica, 50% ether in petroleum ether) provided pure target compound (1.62 g, 88%) as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](OC)O[C@@H]([C@]([C@@H]1OC(C1=CC=CC=C1)=O)(O)C(=S)SC)COC(C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m4_m2:CC(C)(C#N)N=NC(C)(C)C#N, amount is: 0.0 ;m3:C(CCC)[SnH](CCCC)CCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)(=O)O[C@H]1[C@@H](OC)O[C@@H](C[C@@H]1OC(C1=CC=CC=C1)=O)COC(C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of the crude methyl 2,3,6-tri-O-benzoyl-4-(methylthio)thiocarbonyl-α-D-glucopyranoside (5.70 g, 9.55 mmol) in 120 mL of dry toluene was added AIBN (50 mg). Tributyl tin hydride (6.68 mL, 24.8 mmol) was added and the reaction was heated to reflux for 4 hours. The toluene was removed under reduced pressure. Acetonitrile (200 mL) was added and the mixture extracted with petroleum ether (5×100 mL) to remove all tin salts. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to yield a clear colorless oil which solidified on standing. Purification by flash column chromatography using 20% ethyl acetate in petroleum ether as the eluant gave the target compound as a white solid. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C(C)(=O)O[C@@H]1[C@H](OC(C2=CC=CC=C2)=O)[C@@H](OC(C2=CC=CC=C2)=O)C[C@H](O1)COC(C1=CC=CC=C1)=O, amount is: 0.0 ;m1_m4_m2_m3:Br, amount is: 0.0 MOLE;m1_m4_m2_m3:C(C)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 ;m1_m4_m2_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Br[C@@]1(O)[C@H](OC(C2=CC=CC=C2)=O)[C@@H](OC(C2=CC=CC=C2)=O)C[C@H](O1)COC(C1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 1-O-acetyl-2,3,6-tri-O-benzoyl-4-deoxy-α-D-glucopyranose (0.137 g, 0.29 mmol) in 3.0 mL of dry dichloromethane at 0° C. was added 30% hydrogen bromide in acetic acid (0.07 mL, 0.33 mmol). The solution was stirred under argon at room temperature for 4 hours, diluted with ethyl acetate (100 mL) and extracted with a saturated solution of sodium bicarbonate. The organic layer was washed with a saturated solution of sodium chloride, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield the target compound as a colorless oil which solidified upon standing. Crystallization from ether and petroleum ether gave the target compound as white crystals (0.15 g, 100%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:NCCCCCO, amount is: 0.0 ;m1_m3_m2:C(=O)(OCC)N1C(C=2C(C1=O)=CC=CC2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(C=2C(C(N1CCCCCO)=O)=CC=CC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 5-amino-1-pentanol (5.00 g, 48.5 mmol) in benzene (150 mL) was added N-carboethoxyphthalimide (11.0 g, 50.2 mmol) and the solution was stirred at room temperature for 5 h). The solvents were removed under reduced pressure to yield a yellow oil. Purification by flash column chromatography using 25% ethyl acetate in petroleum ether yielded the target compound as a clear colorless oil (9.6 mg, 84%). |
Here is a chemical reaction formula: Reactants are m1_m4_m2:COC=1C=CC=2C(C3=CC=C(C=C3OC2C1C=O)OC)(C)C, amount is: 0.0 ;m1_m4_m2:C(OCC)(OCC)OCC, amount is: 0.0 ;m3:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C1=C(C=CC=2C(C3=CC=C(C=C3OC12)OC)(C)C)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 24.15 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde in 50 ml of absolute ethanol was treated with 50 ml of triethyl orthoformate. After the addition of 100 mg of p-toluenesulphonic acid monohydrate the mixture was boiled under reflux for 1 hour, then cooled and poured into ice-cold sodium bicarbonate solution, whereupon the mixture was extracted twice with 200 ml of ether each time. The combined extracts were washed neutral with water, dried over Na2SO4 and concentrated. The residue was purified on silica gel with hexane/ethyl acetate, whereby there were obtained 19.6 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde dimethyl acetal as a pale yellow oil which crystallized slowly; m.p. 60°-62°, IR 2972, 1606, 1572, 1490 cm-1. |
Here is a chemical reaction formula: Reactants are m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m2_m3:Cl.NO, amount is: 0.0 ;m1_m4_m5_m6:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OC)C=O)OC)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 ;m1_m4_m5_m6:CO, amount is: 0.0 ;m1_m4_m5_m6:C1CCOC1, amount is: 0.0 ;m1_m4_m5_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OC)C=NO)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 g (13.5 mmol) of methyl 3,6-dimethoxy-9,9-dimethyl-5-formylxanthene-4-acetate were dissolved in a mixture of 75 ml of methanol, 75 ml of THF and 20 ml of water. After the addition of 1.66 g of sodium acetate and 1.4 g of hydroxylamine hydrochloride the mixture was stirred at room temperature overnight and then diluted with 200 ml of water. The precipitated solid was filtered off, washed with water and dried, whereby 4.95 g of methyl 3,6-dimethoxy-9,9-dimethyl-5-[(hydroximino)methyl]xanthene-4-acetate were obtained as a white powder of m.p. 234°-236°; IR 1743, 1629, 1604, 1582, 1498 cm-1. |
Here is a chemical reaction formula: Reactants are m5_m3_m6:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ;m1_m4:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, amount is: 0.0 ;m2:C(C1=CC=CC=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3_m6:C(Cl)Cl, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,Catalysts are m5_m3_m6:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3 g (6.55 mmol) of 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid in 65 ml of methylene chloride was cooled to 20° and treated with 1.1 ml (10.62 mmol) of benzyl alcohol. After the addition of 20 mg of 4-dimethylaminopyridine a solution of 1.5 g (7.27 mmol) of dicyclohexylcarbodiimide in 16 ml of methylene chloride was added dropwise, whereupon the mixture was warmed to room temperature and was stirred for 3 hours. The precipitated dicyclohexylurea was filtered off and washed with a small amount of methylene chloride. The filtrate was washed with sodium bicarbonate solution and water, dried over sodium sulphate and concentrated. The residue remaining was chromatographed on silica gel with hexane/ethyl acetate, whereby 2.9 g of benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate were obtained as a colourless powder m.p. of 139°-141°; IR 3443, 2972, 2930, 1724, 1605, 1498 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.9 g (5.29 mmol) of benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate were taken up in a mixture of 10 ml of trifluoroacetic acid and 5 ml of water at 0°. After half an hour the solvents were removed, whereupon the residue was treated with 20 ml of ether. The resulting solid was filtered off, washed with ether and dried over magnesium sulphate, whereby 2.25 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate were obtained as a colourless powder of m.p. 169.5°-171°; IR 1716, 1662, 1631, 1604, 1538, 1494 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2 g (3.56 mmol) of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate in 70 ml of methanol was stirred at room temperature under hydrogen in the presence of 200 mg of palladium/charcoal (10%). After 30 minutes the catalyst was filtered off and the filtrate was concentrated. The residue was washed with ether and dried, whereby 1.6 g of 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid trifluoroacetate of m.p. 178°-184° (dec.) were obtained; IR 1680, 1630, 1608, 1496 cm-1 absorbed., |
Here is a chemical reaction formula: Reactants are m1_m4_m5_m2_m3:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, amount is: 0.0 ;m1_m4_m5_m2_m3:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N1C(CCC1=O)=O, amount is: 0.0 ;m1_m4_m5_m2_m3:C(C)N(C(C)C)C(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m5_m2_m3:O1CCOCC1, amount is: 0.0 ;m1_m4_m5_m2_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.58 g (34.35 mmol) of 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid trifluoroacetate were suspended in a mixture of 7 ml of dioxan and 7 ml of water together with 1.13 g (3.35 mmol) of N-(9-fluorenylmethoxycarbonyl)-succinimide, whereupon 0.9 ml (5.03 mmol) of ethyldiisopropylamine was added at 0°. The mixture was stirred at 0° for 2 hours and thereafter at room temperature for 4 hours. The solid obtained was filtered off, washed with water, dried and chromatographed on silica gel with chloroform/methanol. The fractions containing the desired product were combined, washed with dilute potassium hydrogen sulphate solution and thereafter with water, dried over magnesium sulphate and concentrated, whereby 1.17 g of 5-[(9-fluorenylmethoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid were obtained as a colourless powder of m.p. 134°-136°; IR 1727, 1703, 1606, 1495 cm-1. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)O, amount is: 0.0 ;m1_m5:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m3_m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C, amount is: 0.0 ;m3_m4:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.35 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate in 70 ml of acetonitrile was cooled to 0° and treated with 0.15 g of N-benzyloxycarbonyl-L-alanine. A total of 0.36 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate and 0.17 g of sodium bicarbonate were added in several portions. The reaction mixture was stirred for a total of 36 hours and thereby warmed to room temperature, whereupon it was diluted with ice-water and extracted with methylene chloride. The organic phase was washed with water, dried over magnesium sulphate and concentrated. The residue was chromatographed several times over silica gel in chloroform/methanol, whereby 0.33 g of benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained as a colourless foam; IR 1728, 1673, 1605, 1494 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C(F)(F)F)O, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 MOLE.Products are 0:N[C@@H](C)C(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.3 g of benzyl 5-[(N-benzyloxycarbonyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 85 ml of trifluoroethanol was stirred under hydrogen for 15 minutes in the presence of palladium/charcoal (10%). The catalyst was filtered off and rinsed with trifluoroethanol. The filtrate and wash solution were brought to dryness and the combined residue was chromatographed over silica gel in chloroform/methanol/water, whereby 0.18 g 5-(L-alanylaminomethyl)-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid was obtained as a colourless foam, IR 3450-2400, 1679, 1606, 1575, 1493 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC(=O)N[C@@H]([C@H](OC(C)(C)C)C)C(=O)NCC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 MOLE,Catalysts are m1_m3_m2:[Pd], amount is: 0.0 .Products are 0:COC=1C=CC=2C(C3=CC=C(C=C3OC2C1CC(=O)O)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.67 g (0.84 mmol) of benzyl 5-[(N-benzyloxycarbonyl-O-tert-butyl-L-threonyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 100 ml of e methanol was treated with 140 mg of palladium/charcoal (10%) and stirred under hydrogen for 1. hour. Thereafter, the catalyst was filtered off and the filtrate was brought to dryness. 0.46 g of 5-[O-tert-butyl-L-threonyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid was obtained as the residue in the form of a colourless amorphous powder; IR 3400-2500, 1675, 1606, 1578, 1531, 1493 cm-1. |
Here is a chemical reaction formula: Reactants are m4:C(C)N(C(C)C)C(C)C, amount is: 0.0 ;m1_m5:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC1=CC=C(C=C1)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)O, amount is: 0.0 ;m2_m3:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m2_m3:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OCC1=CC=CC=C1)CNC([C@@H](NC([C@@H](NC([C@@H](NC(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)[C@@H](C)CC)=O)CC1=CC=C(C=C1)OC(C)(C)C)=O)C)=O)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.52 g (0.8 mmol) of N-(9H-fluoren-9-ylmethoxycarbonyl)-L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanine in 20 ml of dimethylformamide was cooled to 0° and treated with 0.45 g (0.8 mmol) of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate and with 0.45 g (1.2 mmol) of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate. Thereafter, 0.31 g (2.4 mmol) of ethyldiisopropylamine was added, whereupon the reaction mixture obtained was warmed from 0° to room temperature within 3 hours and concentrated. The residue remaining was taken up in chloroform, whereupon the solution obtained was washed with water and dried over magnesium sulphate. After chromatography over silica gel (chloroform) 0.77 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(N-(9H-fluoren-9-ylmethoxycarbonyl)-L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate of m.p. 218°-220° was obtained; IR 1728, 1662, 1606, 1503, 1492 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OCC1=CC=CC=C1)CNC([C@@H](NC([C@@H](NC([C@@H](NC(=O)OCC1C2=CC=CC=C2C=2C=CC=CC12)[C@@H](C)CC)=O)CC1=CC=C(C=C1)OC(C)(C)C)=O)C)=O)OC)(C)C, amount is: 0.0 ;m1_m3_m2:C(C)NCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OCC1=CC=CC=C1)CNC([C@@H](NC([C@@H](NC([C@@H](N)[C@@H](C)CC)=O)CC1=CC=C(C=C1)OC(C)(C)C)=O)C)=O)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.74 g (0.73 mmol) of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(N-(9H-fluoren-9-ylmethoxycarbonyl)-L-iso-leucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate in 7 ml of dimethylformamide was stirred at 0° for 1 hour in the presence of 0.7 ml of diethylamine. The reaction mixture was brought to dryness. The residue obtained was chromatographed over silica gel in chloroform/methanol, whereby 0.53 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate was obtained; IR 3292, 2970, 1742, 1672, 1655, 1627, 1605, 1536, 1502, 1499 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OCC1=CC=CC=C1)CNC([C@@H](NC([C@@H](NC([C@@H](N)[C@@H](C)CC)=O)CC1=CC=C(C=C1)OC(C)(C)C)=O)C)=O)OC)(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)O)CNC([C@@H](NC([C@@H](NC([C@@H](N)[C@@H](C)CC)=O)CC1=CC=C(C=C1)OC(C)(C)C)=O)C)=O)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.27 g of benzyl 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetate in 15 ml of methanol was treated with 50 mg of palladium/charcoal (10%) and stirred under hydrogen for 3 hours. After filtering off the catalyst the solvent was removed and the residue was washed with ether. 0.24 g of 3,6-dimethoxy-9,9-dimethyl-5-[(L-isoleucyl-O-tert-butyl-L-tyrosyl-L-alanyl)aminomethyl]xanthene-4-acetic acid of m.p. 146°-149° was obtained; IR 1662, 1606, 1506, 1494 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:COC=1C=CC=2C(C3=CC=C(C=C3OC2C1CC(=O)[O-])OC)(C)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3:FC(C(C(F)(F)F)O)(F)F, amount is: 0.0 ,Catalysts are m4:[Pd], amount is: 0.0 .Products are 0:C1=CC=C(C=2OC3=CC=CC=C3CC12)CC(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 100 mg of benzyl 5-[(N-benzyloxycarbonyl-L-valyl-L-alanyl-L-alanyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucyl-L-alanyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate (benzyl 5-[(N-benzyloxycarbonyl-SEQ ID NO:9)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate) were dissolved in 200 ml of hexafluoroisopropanol, treated with 60 mg of palladium on calcium carbonate (10%) and stirred under hydrogen for 3 hours. After filtering the catalyst the filtrate was concentrated. The residue remaining was washed several times with methanol and thereafter chromatographed over silica gel in chloroform/methanol/hexafluoroisopropanol, whereby 65 mg of 3,6-dimethoxy-9,9-dimethyl-5-[(L-valyl-L-alanyl-L-alanyl-L-phenylalanyl-L-leucyl-L-alanyl-L-leucyl-L-alanyl)aminomethyl]xanthene-4-acetic acid (3,6-dimethoxy-9,9-dimethyl-5-[(SEQ ID NO:9)aminomethyl]xanthene-4-acetic acid) were obtained; IR 3393, 3288, 2963, 1685, 1636, 1531 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m2_m6_m3_m4:FC(C(=O)O)(F)F.NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m6_m3_m4:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@H](CC(=O)OC(C)(C)C)C(=O)O, amount is: 0.0 ;m1_m2_m6_m3_m4:F[B-](F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C, amount is: 0.0 ;m1_m2_m6_m3_m4:C(C)(C)N(CC)C(C)C, amount is: 0.0 ;m5:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m6_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@H](CC(OC(C)(C)C)=O)C(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.17 g of benzyl 5-aminomethyl-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate trifluoroacetate and 0.14 g of N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartic acid in 5 ml of dimethylformamide was treated, with 0.11 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate and with 0.11 ml of diisopropylethylamine. The mixture was stirred at room temperature for 1 hour and thereafter poured into dilute sodium bicarbonate solution. The resulting precipitate was filtered off, washed with water KHSO4 /K2SO4 solution and again with water and dried with 40° in a vacuum, whereby 0.25 g of benzyl 5-[(N-(9-fluorenylmethoxycarbonyl)-4-O-tert-butyl-D-aspartyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained; MS: 841.5 (M+H)+. |
Here is a chemical reaction formula: Reactants are m2_m5:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C, amount is: 0.0 ;m1_m4_m6:COC=1C=CC=2C(C3=CC=C(C=C3OC2C1CC(=O)[O-])OC)(C)C, amount is: 0.0 MOLE;m1_m4_m6:C(C(F)(F)F)O, amount is: 0.0 ;m3:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m5:CN(C=O)C, amount is: 0.0 ,Catalysts are m1_m4_m6:[Pd], amount is: 0.0 MOLE.Products are 0:FC(C(=O)O)(F)F.COC=1C=CC=2C(C3=CC=C(C=C3OC2C1)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.47 g of benzyl 5-[(Nα -benzyloxycarbonyl-NG -(2,2,5,7,8-pentamethylchroman-6-sulphonyl)-L-arginylglycyl-4-O-tert-butyl-L-aspartyl-L-valyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 25 ml of trifluoroethanol was stirred under hydrogen for 2 hours in the presence of palladium/charcoal (10%). Thereafter, the catalyst was filtered off and the filtrate was brought to dryness. The residue was taken up in 20 ml of dimethylformamide together with 0.34 ml of diisopropylethylamine. The solution obtained was added dropwise within 20 minutes to a solution of 0.66 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate in 50 ml of dimethylformamide, whereupon the mixture was stirred at room temperature for 1 hour. Subsequently, the majority of the solvent was removed in a vacuum, whereupon the concentrate obtained was poured into dilute sodium bicarbonate solution. The resulting precipitate was filtered off, washed with water and dried. This crude product was dissolved in a mixture of 20 ml of trifluoroacetic acid, 0.5 ml of water and 0.2 ml of phenol. The solution was left to stand at room temperature for 1 hour and then concentrated. The residue remaining was digested with ether and lyophilized from glacial acetic acid. After purification by HPLC (C-18 phase; gradient: water/ethanol with 0.1% trifluoroacetic acid) 75 mg of 4,5-cyclo-[acetyl-L-arginyl-glycyl-L-aspartyl-L-valyl-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate (4,5-cyclo-[acetyl-SEQ ID NO:2-aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene trifluoroacetate) were is obtained; IR 3364, 2965, 2841, 1664, 1577 and 1497 cm-1 ; MS: 767 (M+H)+. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C1=CC=CC=C1)OC(=O)N[C@@H](C)C(=O)N[C@@H]([C@H](OC(C)(C)C)C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:O1CCOCC1, amount is: 0.0 ,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:N[C@@H](C)C(=O)N[C@@H]([C@H](OC(C)(C)C)C)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 70 mg of methyl 5-[(N-benzyloxycarbonyl-L-alanyl-O-tert-butyl-L-threonyl-L-valyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate in 20 ml of dioxan was treated with 47 mg of palladium/charcoal (10%) and stirred under hydrogen for 19 hours. After filtering off the catalyst the filtrate was concentrated, whereby 59 mg of colourless methyl 5-[(L-alanyl-O-tert-butyl-L-threonyl-L-valyl-glycyl)aminomethyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate was obtained; IR 3300, 2970, 1741, 1680, 1658, 1631, 1523, 1494 cm-1. |
Here is a chemical reaction formula: Reactants are m3:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)OC(=[N+](C)C)N(C)C, amount is: 0.0 ;m4:C(C)(C)N(CC)C(C)C, amount is: 0.0 ;m1_m2_m6:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, amount is: 0.0 ;m1_m2_m6:Cl.C(C1=CC=CC=C1)OC([C@@H](N)CCC(N)=O)=O, amount is: 0.0 ;m5:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(CC[C@H](N)C(=O)NC(CC1=C(C=CC=2C(C3=CC=C(C(=C3OC12)CNC(=O)OC(C)(C)C)OC)(OC)OC)OC)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 0.46 g of 5-[(1-tert-butoxyformamido)-methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid and 0.3 g of O-benzyl-L-glutamine hydrochloride in 10 ml of dimethylformamide was cooled to 0° and treated firstly with 0.45 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate and then with 0.37 ml of diisopropylethylamine. The solution obtained was warmed to room temperature, stirred for 2 hours and then poured into dilute sodium bicarbonate solution. The separated precipitate was filtered off, washed with water and dried in a vacuum, whereby 0.59 g of 5-[N-(tert-butyloxycarbonyl)aminomethyl]-3,6-dimethoxy-9,9-dimethoxyxanthene-4-acetic acid (O-benzyl-L-glutamyl)amide was obtained; MS: 676 (M+H)+. |
Here is a chemical reaction formula: Reactants are m2_m3_m4_m5:[Si](C)(C)(C(C)(C)C)OCC1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)CO, amount is: 0.0 ;m2_m3_m4_m5:C1(C=2C(C(N1)=O)=CC=CC2)=O, amount is: 0.0 ;m2_m3_m4_m5:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m4_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[Si](C)(C)(C(C)(C)C)OCC1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)CN1C(C2=CC=CC=C2C1=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.62 ml (10.34 mmol) of diethyl azodicarboxylate were slowly added dropwise while cooling with ice and under argon to a solution of 3.09 g (7.97 mmol) of [6-(tert-butyl-dimethylsilanyloxymethyl)-10-methyl-phenothiazin-4-yl]-methanol, 1.76 g (11.9 mmol) of phthalimide and 2.30 g (8.75 mmol) of triphenylphosphine in 65 ml of tetrahydrofuran. The reaction mixture was stirred at 0° for 3 hours and then worked-up analogously to that described in Example 2.1.1.ea. The residue was chromatographed on 500 g of silica gel with toluene/ethyl acetate (19:1), whereupon, after crystallization from ethanol/ethyl acetate, 3.22 g (78.2%) of 2-[6-(tert-butyl-dimethylsilanyloxymethyl)-10-methyl-phenothiazin-4-ylmethyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as a light yellow solid of m.p. 195°-196°. |
Here is a chemical reaction formula: Reactants are m2:CSCS(=O)C, amount is: 0.0 ;m1:C(C)OC(C1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)C=O)OCC, amount is: 0.0 ;m4:C(=O)C1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)CC(=O)OC, amount is: 0.0 MOLE;m6:Cl.NO, amount is: 0.0 MOLE;m7:N(O)=CC1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)CC(=O)OC, amount is: 0.0 MOLE;m3:Cl.C(C1=CC=CC=C1)[N+](C)(C)C, amount is: 0.0 MOLE;m5:C(C)(=O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m12:Cl, amount is: 0.0 MOLE;m8:O1CCCC1, amount is: 0.0 ;m14:O1CCCC1, amount is: 0.0 MOLE;m11:CO, amount is: 0.0 MOLE;m10:CO, amount is: 0.0 MOLE;m15:O, amount is: 0.0 MOLE;m9:CO, amount is: 0.0 MOLE,Catalysts are m13:[Pd], amount is: 0.0 MOLE.Products are 0:Cl.NCC1=C2SC=3C(=CC=CC3N(C2=CC=C1)C)CC(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 500 mg (1.46 mmol) of 6-diethoxymethyl-10-methyl-phenothiazine-4-carbaldehyde in 5 ml of tetrahydrofuran can be converted analogously to that described in Example 1.1.1.d with 0.22 g (1.75 mmol) of methyl (methylthiomethyl) sulphoxide, 0.14 ml of TRITON B (benzyltrimethylammonium hydrochloride) solution (35% in methanol) and hydrolysis into methyl 6-formyl-10-methyl-phenothiazine-4-acetate. This compound can be converted analogously to that described in Example 1.1.1.e in methanol, water and tetrahydrofuran using sodium acetate and hydroxylamine hydrochloride into methyl 6-[(hydroximino)methyl]-10-methyl-phenothiazine-4-acetate. This compound can be hydrogenated over palladium/charcoal in methanol and methanolic hydrochloric acid (20%) analogously to that described in Example 1.1.1.f, whereby there is obtained methyl 6-aminomethyl-10-methyl-phenothiazine-4-acetate hydrochloride which can be converted analogously to that described in Example 1.1.2 in dioxan and 1N sodium hydroxide solution using di-tert-butyl dicarbonate into methyl 6-[(1-tert-butylformamido)methyl]-10-methyl-phenothiazine-4-acetate. The product obtained can be hydrolyzed with 1N potassium hydroxide solution in methanol analogously to that described in Example 1.1.3 to give (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetic acid prepared according to Example 2.1.1.g. |
Here is a chemical reaction formula: Reactants are m1:[N+](=[N-])=C, amount is: 0.0 ;m2_m3:C(C)(C)(C)OC(=O)C1=C2SC=3C(=CC=C(C3N(C2=CC=C1)C)CN)CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)C1=C2SC=3C(=CC=C(C3N(C2=CC=C1)C)CN)CC(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1 ml of diazomethane solution (~0.3N in diethyl ether) was added dropwise while cooling with ice to a solution of 80 mg (0.19 mmol) of (6-tert-butoxycarbonyl-aminomethyl-10-methylphenothiazin-4-yl)-acetic acid in 4 ml of methylene chloride. The reaction mixture was brought to room temperature, stirred for 1.5 hours and evaporated. The residue was crystallized from ethyl acetate/hexane, whereupon, after drying in a high vacuum, 72 mg (91%) of methyl (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetate were obtained as a white solid. MS 414 (M+, 64), 358 (100), 343 (15), 314 (15), 238 (15), 57 (16). |
Here is a chemical reaction formula: Reactants are m1:C(C)(C)(C)[Li], amount is: 0.0 ;m5_m6:Cl, amount is: 0.0 ;m4:C(=O)N1CCCCC1, amount is: 0.0 ;m2:C(CCCCC)N1C2=CC=CC=C2SC=2C=CC=CC12, amount is: 0.0 ;m3:CN(C)CCN(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6:C(C)(=O)OCC, amount is: 0.0 ;m7:C(C)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CCCCC)N1C2=CC=CC=C2SC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 38.6 ml of tert-butyllithium solution (1.4M in hexane) were slowly added dropwise at -78° under argon and while stirring to a solution of 11.80 g (41.6 mmol) of 10-hexyl-phenothiazine in 125 ml of abs. diethyl ether and 12.5 ml of N,N,N,N-tetramethylethylenediamine. The reaction mixture was stirred at -75° for 16 hours, brought slowly to 0°, treated with 6.92 ml (1.5 eq.) of N-formylpiperidine, stirred at 0° for 1 hour and then poured into ice, 100 ml of 0.1N hydrochloric acid solution and 250 ml of ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 1 kg of silica gel with ethyl acetate/hexane (1:1), whereupon 6.33 g (48.8%) of 10-hexyl-phenothiazine-4-carbaldehyde were obtained as a light yellowish oil. IR (film): 3064w, 2927m, 2854m, 2731w, 1689s, 1561m, 1455s, 1388w, 1336m, 1286m, 1259s, 1052w, 784m, 750m, 724m. |
Here is a chemical reaction formula: Reactants are m1:S(=O)(=O)(OC)OC, amount is: 0.0 ;m4:O, amount is: 0.0 ;m2_m3_m5_m6:C1=CC2=C(C=C1O)OC3=CC(=O)C=CC3=N2, amount is: 0.0 ;m2_m3_m5_m6:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m5_m6:O1CCOCC1, amount is: 0.0 ,Catalysts are m2_m3_m5_m6:COCCOCCN(CCOCCOC)CCOCCOC, amount is: 0.0 MOLE.Products are 0:COC1=CC2=C(C=C1)N=C3C=CC(=O)C=C3O2, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 12.1 ml of dimethyl sulphate were added at room temperature while stirring well to a suspension of 20.0 g (85.0 mmol) of resorufin, 17.6 g of freshly powdered potassium carbonate and 10 drops of tris-[2-(2-methoxyethoxy)ethyl]amine in 150 ml of dioxan. The reaction mixture was subsequently stirred at 100° for 2 hours, cooled and then treated with 150 ml of water. The solid was filtered off, washed with water and dried over phosphorus pentoxide. 11.5 g (59.5%) of resorufin methyl ether of m.p. 240°-244° (dec.) were obtained. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(C=2C(C(N1)=O)=CC=CC2)=O, amount is: 0.0 ;m1_m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m4_m6:[N+](=[N-])(C(=O)OCC)C(=O)OCC, amount is: 0.0 ;m3_m5:COC=1C=CC2=C(OC3=C(N2C)C=CC(=C3COCOCCOC)OC)C1CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m6:O1CCCC1, amount is: 0.0 ;m3_m5:O1CCCC1, amount is: 0.0 ;m10_m9_m8_m7:C(C)(=O)OCC, amount is: 0.0 ;m10_m9_m8_m7:CO, amount is: 0.0 ;m10_m9_m8_m7:CCCCCC, amount is: 0.0 ;m10_m9_m8_m7:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=C(C2=C(OC3=C(N2C)C=CC(=C3COCOCCOC)OC)C1)CN1C(C3=CC=CC=C3C1=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 1.63 g (1.5 eq.) of phthalimide and 2.91 g (1.5 eq.) of triphenylphosphine were added portionwise while cooling with ice to a solution of 3.0 g (7.40 mmol) of 3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e]-[1,4]oxazine-4-methanol in 40 ml of tetrahydrofuran. Then, a solution of 2.06 g (1.6 eq.) of diethyl diazodicarboxylate in 10 ml of tetrahydrofuran was slowly added dropwise at 0° during 2 hours. The reaction mixture was stirred at 0° for 10 hours and then poured into 50 ml of water, 100 ml of hexane, 50 ml of methanol and 50 ml of ethyl acetate. The organic phase was separated, washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 200 g of silica gel with ethyl acetate/hexane (1:1), whereupon 3.61 g (93.7%) of N-[[3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo-[b,e][1,4]oxazin-1-yl]methyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as an amorphous foam. MS: 534 (M+, 100), 160(8). |
Here is a chemical reaction formula: Reactants are m1_m2:O.NN, amount is: 0.0 ;m1_m2:COC=1C=CC2=C(OC3=C(N2C)C=CC(=C3CN3C(C2=CC=CC=C2C3=O)=O)OC)C1CC#N, amount is: 0.0 ;m4_m3:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4_m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:NCC1=C(C=CC=2N(C3=C(OC21)C(=C(C=C3)OC)CC#N)C)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.0 ml of ethanolic hydrazine hydrate solution (1M) were added at room temperature to a suspension of 280 mg of [3,7-dimethoxy-6-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-ylmethyl)-10-methyl-10H-dibenz[b,e][1,4]-oxazin-4-yl]-acetonitrile. The reaction mixture was heated to 85° for 4 hours, the cooled and poured into methylene chloride and 10% sodium carbonate solution. The aqueous phase was extracted with ethylene chloride and the combined organic fractions were dried over magnesium chloride and concentrated. The residue was dried in a high vacuum and, after recrystallization from tert.-butyl methyl ether/methanol, 180 mg (90.1%) of 6-aminomethyl-3,7-dimethoxy-10-methyl-10H-dibenzo[b,e][1,4]oxazine-4-acetonitrile were obtained as a beige solid of m.p. 167°-169° (dec.). |
Here is a chemical reaction formula: Reactants are m4_m8_m7:O, amount is: 0.0 ;m2_m3_m6:C(C)OC=1C=CC2=C(OC3=C(N2CC)C=CC(=C3)OCC)C1CO, amount is: 0.0 ;m2_m3_m6:N1C=NC=C1, amount is: 0.0 ;m1_m5:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m8_m7:CCCCCC, amount is: 0.0 ;m4_m8_m7:C(C)OCC, amount is: 0.0 ;m2_m3_m6:CN(C=O)C, amount is: 0.0 ;m1_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1=CC=CC=2OC3=C(NC21)C=CC=C3, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.92 g (1.3 eq.) of tert-butyldimethylsilyl chloride in 10 ml of N,N-dimethylformamide was added dropwise while cooling with ice to a mixture of 3.23 g (9.80 mmol) of 3,7-diethoxy-10-ethyl-10H-dibenzo[b,e][1,4]oxazine-4-methanol and 1.47 g (2.2 eq.) of imidazole in 30 ml of N,N-dimethylformamide. The reaction mixture was stirred at 0° for 30 minutes, brought slowly to room temperature, stirred for 1 hour and then poured into 100 ml of water, 50 ml of diethyl ether and 50 ml of hexane. The organic phase was separated, extracted twice with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on 250 g of silica gel with diethyl ether/hexane (1:10), whereupon, after drying in a high vacuum, 4.30 g (98.9%) of 10-methyl-3,7-diethoxyl-4-[(tert-butyl-dimethylsilyl)oxy]methyl!-10H-dibenzo[b,e][1,4]oxazine were obtained as a colourless solid of m.p. 77.5°-78.5°. |
Here is a chemical reaction formula: Reactants are m4_m7:COC=1C=CC=2N(C3=CC=C(C(=C3SC2C1C=O)COCOCCOC)OC)C, amount is: 0.0 MOLE;m1_m6_m2_m3:COC=1C=CC=2N(C3=CC=C(C=C3SC2C1COCOCCOC)OC)C, amount is: 0.0 ;m1_m6_m2_m3:C(CCC)[Li], amount is: 0.0 ;m1_m6_m2_m3:C(=O)N1CCCCC1, amount is: 0.0 ;m5:[BH4-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7:O1CCCC1, amount is: 0.0 ;m1_m6_m2_m3:C(C)OCC.O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC=2N(C3=CC=C(C(=C3SC2C1CO)COCOCCOC)OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 8.31 g (21.73 mmol) of 3,7-dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazine in 100 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 17.6 ml of n-butyllithium solution (1.6M in hexane) and 3.68 g (32.6 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The resulting 3,7-dimethoxy-6-(2-methoxyethoxymethoxymethyl)-10-methylphenothiazine-4-carbaldehyde was dissolved in 100 ml of tetrahydrofuran and reduced with 22 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.8.b. The crude product was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying in a high vacuum, 6.44 g (70.3%) of [3,7-dimethoxy-6-(2-methoxy-ethoxymethoxymethyl)-10-methyl-phenothiazin-4-yl]-methanol were obtained as light yellowish oil. |
Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:C(CCCCC)N1C2=CC=C(C=C2SC=2C=C(C=CC12)OC)OC, amount is: 0.0 ;m1_m4_m2_m3:C(CCC)[Li], amount is: 0.0 ;m1_m4_m2_m3:C(=O)N1CCCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(C)OCC.O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCCCC)N1C2=CC=C(C=C2SC=2C(=C(C=CC12)OC)C=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3.42 g (10.0 mmol) of 10-hexyl-3,7-dimethoxy-phenothiazine in 50 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 8.12 ml of n-butyllithium solution (1.6M in hexane) and 3.35 g (29.6 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The product was chromatographed on silica gel with ethyl acetate/hexane (1:4), whereupon 2.39 g (64.4%) of 10-hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde were obtained as a red oil. |
Here is a chemical reaction formula: Reactants are m3_m4_m5:C(CCCCC)N1C2=CC=C(C=C2SC=2C(=C(C=CC12)OC)CO)OC, amount is: 0.0 MOLE;m3_m4_m5:C(CCC)[Li], amount is: 0.0 ;m3_m4_m5:COCCOCCl, amount is: 0.0 ;m1:C(CCCCC)N1C2=CC=C(C=C2SC=2C(=C(C=CC12)OC)C=O)OC, amount is: 0.0 ;m2:[BH4-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O1CCCC1, amount is: 0.0 ;m7_m0:C(C)OCC.CCCCCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCCCC)N1C2=CC=C(C=C2SC=2C(=C(C=CC12)OC)COCOCCOC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.39 g (6.43 mmol) of 10-hexyl-3,7-dimethoxy-phenothiazine-4-carbaldehyde in 30 ml of tetrahydrofuran was reduced with 7.0 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.1.da. The resulting 10-hexyl-3,7-dimethoxyphenothiazine-4-methanol was reacted with 4.0 ml of n-butyllithium solution (1.6M in hexane) and 1.0 g (8.0 mmol) of 2-methoxyethoxymethyl chloride analogously to that described in Example 4.1.1.db. After chromatography on silica gel with diethyl ether/hexane (3:2) 2.33 g (78.5%) of 10-hexyl-3,7-dimethoxy-4-(2-methoxyethoxymethoxymethyl)-phenothiazine were obtained as a light yellowish oil. |
Here is a chemical reaction formula: Reactants are m1_m6_m2_m3:C(CCCCC)N1C2=CC=C(C=C2SC=2C(=C(C=CC12)OC)COCOCCOC)OC, amount is: 0.0 ;m1_m6_m2_m3:C(CCC)[Li], amount is: 0.0 ;m1_m6_m2_m3:C(=O)N1CCCCC1, amount is: 0.0 ;m4_m7:COC=1C=CC=2N(C3=CC=C(C(=C3SC2C1C=O)COCOCCOC)OC)CCCCCC, amount is: 0.0 MOLE;m5:[BH4-].[Li+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2_m3:C(C)OCC.O1CCCC1, amount is: 0.0 ;m4_m7:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CCCCC)N1C2=CC=C(C(=C2SC=2C(=C(C=CC12)OC)CO)COCOCCOC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 8.0 g (17.33 mmol) of 10-hexyl-3,7-dimethoxy-4-(2-methoxy-ethoxymethoxymethyl)-phenothiazine in 100 ml of diethyl ether/tetrahydrofuran (4:1) was reacted with 12.0 ml of n-butyllithium solution (1.6M in hexane) and 2.94 g (26.0 mmol) of N-formylpiperidine analogously to that described in Example 4.1.1.c. The resulting 3,7-dimethoxy-10-hexyl-6-(2-methoxyethoxymethoxymethyl)phenothiazine-4-carbaldehyde was dissolved in 100 ml of tetrahydrofuran and reduced with 22 ml of lithium borohydride solution (1M in tetrahydrofuran) analogously to that described in Example 4.1.8.b. The product was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying in a high vacuum, 4.41 g (51.7%) of [10-hexyl-3,7-dimethoxy-6-(2-methoxyethoxymethoxymethyl)-phenothiazin-4-yl]-methanol were obtained as a light yellowish oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:FC(C(=O)O)(F)F.NCC1=C2SC=3C(=C(C=CC3N(C2=CC=C1OC)CCCCCC)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m4:N([C@@H](COC(C)(C)C)C(=O)O)C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C12, amount is: 0.0 ;m1_m2_m3_m4:CN(C)C(=[N+](C)C)ON1C2=C(C=CC=C2)N=N1.[B-](F)(F)(F)F, amount is: 0.0 ;m1_m2_m3_m4:CCN(C(C)C)C(C)C, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C1=CC=CC=2C3=CC=CC=C3C(C12)COC(=O)N[C@@H](COC(C)(C)C)C(=O)C(C1=C2SC=3C(=C(C=CC3N(C2=CC=C1OC)CCCCCC)OC)CC(=O)OCC1=CC=CC=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 250 mg of benzyl (6-aminomethyl-3,7-dimethoxy-10-hexyl-phenothiazin-4-yl)-acetate trifluoroacetate (1:1) were reacted with 153 mg of Fmoc-Ser(But)-OH, 141 mg of TBTU and 0.15 ml of DIPEA analogously to that described in Example 4.7.1. 20 mg of benzyl [6-((N-(9H-fluoren-9-ylmethoxycarbonyl)-O-tert.-butyl-L-seryl)-aminomethyl)-10-hexyl-3,7-dimethoxyphenothiazin-4-yl]-acetate were obtained; MS: 886.6 MH⊕. |
Here is a chemical reaction formula: Reactants are m1_m2:FC(C(=O)O)(F)F.NCC1=C2SC=3C(=C(C=CC3N(C2=CC=C1OC)CCCCCC)OC)CC(=O)OCC1=CC=CC=C1, amount is: 0.0 ;m1_m2:N([C@@H](CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)C(C1=C2SC=3C(=C(C=CC3N(C2=CC=C1OC)CCCCCC)OC)CC(=O)OCC1=CC=CC=C1)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 72.8 mg of benzyl (6-aminomethyl-3,7-dimethoxy-10-hexylphenothiazin-4-yl)-acetate trifluoroacetate were reacted with 39.7 mg of Boc-Phe-OH analogously to that described in Example 4.7.1. The crystalline benzyl [6-((N-tert.-butoxycarbonyl-L-phenylalanyl)-aminomethyl)-10-hexyl-3,7-dimethoxyphenothiazin-4-yl]-acetate obtained was dissolved in trifluoroacetic acid, whereupon the solution was left to stand at 20° for 10 minutes and concentrated in a vacuum. The residue was dissolved in 3 ml of DMF, whereupon 84.3 mg of Z-Tyr(Bzl)-ONp were added and the pH value was adjusted to 8.5 with DIPEA. After 3 hours the reaction mixture was worked up as described in Example 4.7.1. The crystalline benzyl [6-(((N,O-bis-benzyloxycarbonyl-L-tyrosyl)-L-phenylalanyl)-aminomethyl)-10-hexyl-3,7-dimethoxy-phenothiazin-4-yl]-acetate obtained was further processed analogously to that described in Example 2.2.1., whereby the crude product was crystallized from ethanol. 21.3 mg of 10-hexyl-3,7-dimethoxy-4,6-cyclo-[acetyl-L-tyrosyl-L-phenylalanyl-aminomethyl]phenothiazine were obtained; MS: 723.5 MH+. |
Here is a chemical reaction formula: Reactants are m3:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 ;m1_m4_m2:COC=1C=CC=2C(C3=CC=C(C=C3OC2C1C=O)OC)(C)C, amount is: 0.0 ;m1_m4_m2:C(OCC)(OCC)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C1=C(C=CC=2C(C3=CC=C(C=C3OC12)OC)(C)C)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 24.15 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde in 50 ml of absolute ethanol was treated with 50 ml of triethyl orthoformate. After the addition of 100 mg of p-toluenesulphonic acid monohydrate the mixture was boiled under reflux for 1 hour, then cooled and poured into ice-cold sodium bicarbonate solution, whereupon the mixture was extracted twice with 200 ml of ether each time. The combined extracts were washed neutral with water, dried over Na2SO4 and concentrated. The residue was purified on silica gel with hexane/ethyl acetate, whereby there were obtained 19.6 g of 3,6-dimethoxy-9,9-dimethylxanthene-4-carboxaldehyde dimethyl acetal as a pale yellow oil which crystallized slowly; m.p. 60°-62°, IR 2972, 1606, 1572, 1490 cm-1. |
Here is a chemical reaction formula: Reactants are m1_m4_m5_m6:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OC)C=O)OC)(C)C, amount is: 0.0 ;m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m2_m3:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m7:O, amount is: 0.0 ;m1_m4_m5_m6:CO, amount is: 0.0 ;m1_m4_m5_m6:C1CCOC1, amount is: 0.0 ;m1_m4_m5_m6:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC=1C=CC=2C(C3=CC=C(C(=C3OC2C1CC(=O)OC)C=NO)OC)(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5 g (13.5 mmol) of methyl 3,6-dimethoxy-9,9-dimethyl-5-formylxanthene-4-acetate were dissolved in a mixture of 75 ml of methanol, 75 ml of THF and 20 ml of water. After the addition of 1.66 g of sodium acetate and 1.4 g of hydroxylamine hydrochloride the mixture was stirred at room temperature overnight and then diluted with 200 ml of water. The precipitated solid was filtered off, washed with water and dried, whereby 4.95 g of methyl 3,6-dimethoxy-9,9-dimethyl-5-[(hydroximino)methyl]xanthene-4-acetate were obtained as a white powder of m.p. 234°-236°; IR 1743, 1629, 1604, 1582, 1498 cm-1. |
Here is a chemical reaction formula: Reactants are m5_m3_m6:C1(CCCCC1)N=C=NC1CCCCC1, amount is: 0.0 ;m2:C(C1=CC=CC=C1)O, amount is: 0.0 ;m1_m4:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m3_m6:C(Cl)Cl, amount is: 0.0 ;m1_m4:C(Cl)Cl, amount is: 0.0 ,Catalysts are m5_m3_m6:CN(C1=CC=NC=C1)C, amount is: 0.0 .Products are 0:C(C)(C)(C)OC(=O)NCC1=C2OC=3C(=C(C=CC3C(C2=CC=C1OC)(C)C)OC)CC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3 g (6.55 mmol) of 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid in 65 ml of methylene chloride was cooled to 20° and treated with 1.1 ml (10.62 mmol) of benzyl alcohol. After the addition of 20 mg of 4-dimethylaminopyridine a solution of 1.5 g (7.27 mmol) of dicyclohexylcarbodiimide in 16 ml of methylene chloride was added dropwise, whereupon the mixture was warmed to room temperature and was stirred for 3 hours. The precipitated dicyclohexylurea was filtered off and washed with a small amount of methylene chloride. The filtrate was washed with sodium bicarbonate solution and water, dried over sodium sulphate and concentrated. The residue remaining was chromatographed on silica gel with hexane/ethyl acetate, whereby 2.9 g of benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate were obtained as a colourless powder m.p. of 139°-141°; IR 3443, 2972, 2930, 1724, 1605, 1498 cm-1. |