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Here is a chemical reaction formula: Reactants are:m1_m2:Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2;m1_m2:CNC1=CC=CC=C1, Reagents are:, and Products are 0:CN1CC(OC2=C(C1=O)C=CC=N2)CCN(C2=CC=CC=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepin-5(4H)-one hydrochloride, 4.00 g (0.015 mole) was dissolved in N-methylaniline (30 ml) and heated to 95° C. with stirring for 2 days. Excess N-methylaniline was removed by rotary evaporation (95° C., vacuum pump). The residue was taken up in chloroform (80 ml) and washed with dilute aqueous sodium hydroxide (30 ml). The chloroform layer was decolorized with activated carbon and dried over sodium sulfate, filtered and concentrated by rotary evaporation. The remaining residue was dissolved in ethyl acetate (50 ml) and purified by high pressure liquid chromatography using a silica gel column and ethyl acetate as the eluent. After purification, crystals formed from ethyl acetate. These crystals were recrystallized from ethyl acetate, giving 1.40 g (31%) of pale brown crystals. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2;m1_m3_m2:CC1NCCC1, Reagents are:m1_m3_m2:C(C)O, and Products are 0:CN1CC(OC2=C(C1=O)C=CC=N2)CCN2C(CCC2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3.5 g (0.0145 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in ethanol (15 ml) was added 2-methyl pyrrolidine (5.0 g, 0.063 mole). The solution was heated to reflux for 3 hours with stirring. The ethanol was removed by rotary evaporation (water aspirator, 80° C.). The residual oil was partitioned between dilute aqueous sodium hydroxide (50 ml) and chloroform (50 ml). The organic layer was saved and the aqueous layer extracted with chloroform (2×30 ml). All the chloroform layers were combined, dried over anhydrous sodium sulfate and concentrated by rotary evaporation (water aspirator, 70° C.). The residual oil was then distilled at 200° C. and low vacuum (vacuum pump) giving 1.5 g (36.7%) of a clear oil. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:Cl.ClCCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C;m1_m3_m2:CNC, Reagents are:m1_m3_m2:CO, and Products are 0:Cl.Cl.CN(CCC1(OC2=C(C(N(C1)C)=O)C=CC=N2)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 4.5 g (0.015 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepin-5(4H)-one hydrochloride in 15 ml of methanol was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 8 days. The methanol and dimethylamine were removed by rotary evaporation (70° C.; 30 mm). The residue was taken up in 150 ml of chloroform, washed with 2×50 ml dil aqueous sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation (70° C.; 30 mm). The syrupy residue was treated with hydrogen chloride in isopropyl alcohol, which afforded 3.5 g (67%) of white crystals, m.p. 188°-90° C. |
Here is a chemical reaction formula: Reactants are:m2:CNC;m1_m3:ClCCC1(OC2=C(C(N(C1)C)=S)C=CC=N2)C, Reagents are:m1_m3:CO, and Products are 0:Cl.CN(CCC1(OC2=C(C(N(C1)C)=S)C=CC=N2)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 4.5 g (0.017 mole) of 2-(2-chloroethyl)-2,3-dihydro-2,4-dimethylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 20 ml of methanol, cooled in an ice bath, was added 40 ml of dimethylamine. The flask was sealed tightly and left standing at room temperature for 10 days. The dimethylamine and methanol were removed by rotary evaporation (60° C.; 30 mm). The residue was taken up in 150 ml of chloroform, washed with 3×50 ml dil sodium hydroxide, dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation (70° C.; 30 mm). The crude oil was dissolved in isopropyl alcohol and treated with ethereal hydrogen chloride, which yielded 4.0 g (76%) of yellow crystals, m.p. 255° C. with decomposition. |
Here is a chemical reaction formula: Reactants are:m2:CC1NCCC1;m4:C(\C=C\C(=O)O)(=O)O;m3:C([O-])([O-])=O.[K+].[K+];m1_m5:ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2, Reagents are:m1_m5:C(C)O, and Products are 0:CC(C)O.C(\C=C\C(=O)O)(=O)O.CN1CC(OC2=C(C1=S)C=CC=N2)CCN2C(CCC2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 5.0 g (0.019 mole) of 2-(chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione in 25 ml of absolute ethanol was added 3.5 g (0.04 mole) of 2-methylpyrrolidine. The mixture was heated to reflux for 6.5 hr and left standing at room temperature overnight. Mass spec and TLC showed presence of starting materials. Approximately 5 g of potassium carbonate was added and heating at reflux was continued for 24 hr. Ethanol was removed by rotary evaporation (70° C., 30 mm). The residue was taken up in 100 ml of methylene chloride and washed with 2×50 ml dil. aqueous sodium hydroxide. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation (70° C., 30 mm). The residual syrup was dissolved in isopropyl aocohol and treated with fumaric acid affording 4.5 g (0.01 mole, 49.2%) of crude crystals. Two recrystallizations from isopropyl afforded 1.5 g (16.4%) of yellow crystals, m.p., 92°-95° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:ClCCC1N(C2=C(C(N(C1)CC)=O)C=CC=C2)C;m1_m2:N1CCOCC1, Reagents are:, and Products are 0:C(C)N1CC(N(C2=C(C1=O)C=CC=C2)C)CCN2CCOCC2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 30 g (0.112 mole) of 2-(2-chloroethyl)-4-ethyl-1-methyl-1,2,3,4-tetrahydro-5H-1,4-benzodiazepin-5-one in 70 ml of morpholine was refluxed for 3 hrs, concentrated on the rotary evaporator and the residue partitioned between chloroform and dilute sodium hydroxide. The chloroform was dried over anhydrous sodium sulfate and concentrated on the rotary evaporator. The residue was crystallized twice from isopropyl ether containing a small amount of ethanol, m.p. 128°-148° C. Recrystallization from toluene gave 19.5 g (61%) of product, m.p. 128°-148° C. |
Here is a chemical reaction formula: Reactants are:m1:ClCCC1OC2=C3C=CN=CC3=CC=C2C(N(C1)C)=S;m2:CNC, Reagents are:, and Products are 0:Cl.CN(CCC1OC2=C3C=CN=CC3=CC=C2C(N(C1)C)=S)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[7,6-f]isoquinoline-5(4H)-thione is reacted with dimethylamine to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1:ClCCC1OC2=C(C=C(C=3C=CC=NC23)C)C(N(C1)C)=S;m2:CNC, Reagents are:, and Products are 0:Cl.CN(CCC1OC2=C(C=C(C=3C=CC=NC23)C)C(N(C1)C)=S)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4,7-dimethyl-1,4-oxazepino[6,7-h]quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound. |
Here is a chemical reaction formula: Reactants are:m2:CNC;m1:ClCCC1OC2=C(C=CC=3C=CC(=NC23)C)C(N(C1)C)=S, Reagents are:, and Products are 0:Cl.CN(CCC1OC2=C(C=CC=3C=CC(=NC23)C)C(N(C1)C)=S)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4,10-dimethyl-1,4-oxazepino[6,7-h)quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1:ClCCC1OC=2C(=C3C=CC=NC3=CC2)C(N(C1)C)=S;m2:CNC, Reagents are:, and Products are 0:Cl.CN(CCC1OC=2C(=C3C=CC=NC3=CC2)C(N(C1)C)=S)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 31, 4-(2-chloroethyl)-3,4-dihydro-2-methyl-[1,4]-oxazepino[6,7-f]quinoline-1(2H )-thione is reacted with dimethylamine to give the title compound. |
Here is a chemical reaction formula: Reactants are:m1:ClCCC1OC2=C(C=CC=3C=CC=NC23)C(N(C1)C)=S;m2:CNC, Reagents are:, and Products are 0:Cl.CN(CCC1OC2=C(C=CC=3C=CC=NC23)C(N(C1)C)=S)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 31, 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-h]quinoline-5(4H)-thione is reacted with dimethylamine to give the title compound. |
Here is a chemical reaction formula: Reactants are:m2_m3:C([O-])([O-])=O.[K+].[K+];m2_m3:N1CCC1;m5:N1CCC1;m1_m6:ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2;m1_m6:CS(=O)C;m4:N1CCC1, Reagents are:, and Products are 0:C(\C=C\C(=O)O)(=O)O.N1(CCC1)CCC1OC2=C(C(N(C1)C)=S)C=CC=N2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 5.0 g (0.0914 mole) of 2-(2-chloroethyl)-2,5-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepine-5(4H)-thione dissolved in 50 ml of dimethylsulfoxide was added 8.04 g (0.058 mole) of potassium carbonate and 1.21 g (0.021 mole) of azetidine. The reaction mixture was stirred at room temperature for 8 hr after which was added 0.5 g (0.009 mole) of azetidine and the mixture was stirred overnight at room temperature. An additional 0.3 g (0.005 mole of azetidine was added and stirring was continued for 24 hr. The mixture was filtered and solvent removed by rotary evaporator at 80° C., 0.5 mm Hg. The residue was taken up in 100 ml of chloroform and the solution was washed with two 30 ml portions of dilute aqueous sodium hydroxide. The organic layer was dried over magnesium sulfate, filtered and concentrated by rotary evaporator. The residue was reacted with fumaric acid in isopropyl alcohol to give 2.5 g (31%) of pale yellow crystals, m.p. 122°-126° C. |
Here is a chemical reaction formula: Reactants are:m3:C(C)NCC;m6:C(C)NCC;m4:C(C)OC(C)=O.CO;m1_m7:ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O;m2:C(C)NCC;m5:[OH-].[NH4+], Reagents are:m1_m7:C(C)O, and Products are 0:C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)CCN(CC)CC)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 2.26 ml (0.022 mole) of diethylamine and the mixture heated to reflux. (Complete dissolution occurred). After 1 hr, another 2.26 ml (0.022 mole) of diethylamine was added followed by 5.0 ml (0.049 mole) and heating continued for 2 more hours. TLC (ethylacetate/methanol/conc. ammonium hydroxide, 7:2:1, v/v/v) still showed presence of starting material; another 2.26 ml (0.022 mole) of diethylamine was added and heating continued for 15 hr at reflux. Solvent was removed by rotary evaporation (60° C., 30 mm Hg) and the residue taken up in methylene chloride, washed twice with dilute aqueous sodium hydroxide and once with water. The organic layer was dried over sodium sulfate, filtered and concentrated by rotary evaporation, and azeotroped once with toluene. The oil was treated with oxalic acid in isopropyl alcohol which yielded 6.7 g (76%) of white crystals, m.p. 163°-164° C. |
Here is a chemical reaction formula: Reactants are:m3:C(C1=CC=CC=C1)CN;m4_m6:C(C(=O)O)(=O)O;m1_m5_m2:ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O;m1_m5_m2:C(C1=CC=CC=C1)CN, Reagents are:m4_m6:C(C)(C)O;m1_m5_m2:C(C)O, and Products are 0:C(C(=O)O)(=O)O.ClC1=CC=2C(N(CC(OC2N=C1)NCC1=C(C=CC=C1)C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6.0 g (0.022 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-one in 50 ml of absolute ethanol was added 5.3 g (0.044 mole) of benzylmethylamine and the mixture heated to reflux for three days. The solvent was removed by rotary evaporation, and the residue was taken up in 100 ml of methylene chloride, which was subsequently washed with 2×50 ml of dilute sodium hydroxide and 50 ml water, dried over sodium sulfate, filtered, and concentrated by rotary evaporation. Residual benzylmethylamine was removed at 95° C., 0.5 mm Hg. However, the mass spectrum now showed starting material; therefore, the residue was taken up in 50 ml of absolute ethanol. To the resulting solution was added 2.7 g (0.022 mole) of benzylmethylamine and the mixture heated to reflux for 24 hrs. The reaction mixture was subjected to the same work-up as mentioned before. The syrup was treated with oxalic acid in isopropyl alcohol. The resulting crystals were recrystallized from ethanol/isopropyl alcohol to give 4.7 g (47.9%) of white crystals, m.p. 176°-179° C. |
Here is a chemical reaction formula: Reactants are:m1:S(=O)(=O)=O;m2:S(O)(O)(=O)=O, Reagents are:, and Products are 0:OS(=O)(=O)O.O=S(=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: FIG. 7 depicts a subunit for sulfuric acid. Liquid sulfur dioxide is supplied by a cylinder 121 to a fractionating column 122 and then to a membrane filter 123. The purified sulfur dioxide gas is then fed to a catalytic oxidizer 124 where it is combined with purified air 125 over a platinum or other suitable catalyst to produce sulfur trioxide 126. The sulfur trioxide is combined with purified sulfuric acid 127 in an absorber 128 to form ultra-pure oleum 129, which is subsequently diluted with ultra-pure water 130 in a diluting vessel 131. An electrolysis cell 132 then converts this diluted oleum to a mixture of sulfuric and persulfuric acids 133. recycling some of the sulfuric acid back to the absorber 128. As in the other subunits, the product mixture is ready for application directly to the point of use on the fabrication line. |
Here is a chemical reaction formula: Reactants are:m5_m6_m1_m2_m3:C(C)OC1=CC=C(C=C1)C#C;m5_m6_m1_m2_m3:FC=1C=C(C=CC1F)I;m5_m6_m1_m2_m3:C(C)N(CC)CC, Reagents are:m4:C(C)(C)(C)OC;m5_m6_m1_m2_m3:Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl;m5_m6_m1_m2_m3:[Cu]I, and Products are 0:FC=1C=C(C=CC1F)C#CC1=CC=C(C=C1)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.4 mmol of bis(triphenylphosphine)palladium(II) chloride and 0.2 mmol of CuI are added at room temperature to a mixture of 0.02 m of 4-ethoxyphenylacetylene, 0.02 m of 3,4-difluoroiodobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with 100 ml of methyl tert.-butyl ether and filtered with suction, and the solution is evaporated. Purification by chromatography and/or crystallization gives 3,4-difluoro-4'-ethoxytolan, K 67 I, Δε=11.18. |
Here is a chemical reaction formula: Reactants are:m5_m6_m1_m2_m3:C(CCC)OC1=CC=C(C=C1)C#C;m5_m6_m1_m2_m3:FC=1C=C(C=C(C1F)F)Br;m5_m6_m1_m2_m3:C(C)N(CC)CC, Reagents are:m5_m6_m1_m2_m3:Cl[Pd]([P](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)([P](C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl;m5_m6_m1_m2_m3:[Cu]I;m4:C(C)(C)(C)OC, and Products are 0:FC=1C=C(C=C(C1F)F)C#CC1=CC=C(C=C1)OCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.4 mmol of bis(triphenylphosphine)palladium(II) chloride and 0.2 mmol of CuI are added at room temperature to a mixture of 0.02 m of 4-butoxyphenylacetylene, 0.02 m of 3,4,5-trifluorobromobenzene and 50 ml of triethylamine. The reaction mixture is stirred at room temperature for 2 hours, diluted with methyl tert.-butyl ether and filtered with suction, and the solution is evaporated. Purification by chromatography and/or crystallization gives 3,4,5-trifluoro-4'-butoxytolan. |
Here is a chemical reaction formula: Reactants are:m3_m4:C(#N)C1=CC=C(C=C1)C(C=O)=COC;m1_m5:[Na];m2:Cl.C(N)(=N)C1=CC=C(C(=O)N)C=C1, Reagents are:m3_m4:CO;m1_m5:CO, and Products are 0:C(#N)C1=CC=C(C=C1)C=1C=NC(=NC1)C1=CC=C(C(=O)N)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 247 mg of sodium are treated at room temperature with 10 ml of methanol. After 15 minutes the solution obtained is treated at room temperature with 1.58 g of 4-amidinobenzamide hydrochloride. A white suspension forms and this is treated dropwise at room temperature within 10 minutes with a solution of 1.42 g of 2-(4-cyanophenyl)-3-methoxyacrolein in 50 ml of methanol. The reaction mixture is stirred at room temperature for a further 2 hours and then suction filtered. The residue is washed with water, tetrahydrofuran and diethyl ether and dried in a high vacuum. 4-[5-(4-Cyanophenyl)-2-pyrimidinyl]benzamide is obtained. |
Here is a chemical reaction formula: Reactants are:m1:OC=1C=C2OC3=CC(C(=CC3=NC2=CC1)CCCCCCCCCCCCCCCCCC)=O;m3:CC(=O)OCC1[C@@H]([C@@H](C([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C;m2:CC1=CC(=NC(=C1)C)C, Reagents are:m5:C([O-])([O-])=O.[Ag+2];m4:ClCCl, and Products are 0:C(CCCCCCCCCCCCCCCCC)C1=CC2=NC3=CC=C(C=C3OC2=CC1=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, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7-hydroxy-2-octadecyl-3H-phenoxazine-3-one ("octadecylresorufin) (220 mg, 0.47 mmole), powdered, activated 4Å molecular sieves (0.5 g), sym-collidine (125 μL, 0.95 mmole), and silver carbonate (155 mg, 0.56 mmole) in dry dichloromethane (20 mL) is allowed to stir at room temperature, under an atmosphere of dry nitrogen gas, in the dark for 1 hour. To this mixture is added 1-bromo-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (389 mg, 0.95 mmole), slowly with stirring, and the resulting heterogenous solution allowed to stir as above for 72 hours. After this time the reaction mixture is filtered through a pad of diatomaceous earth. The precipitate is washed with chloroform (5×10 mL) and the combined organic filtrates are extracted with 1M aqueous HCl (1×75 mL), saturated aqueous sodium bicarbonate solution (1×75 mL), 1M sodium thiosulfate (1×75 mL), and water (1×75 mL). The organic layer is dried over anhydrous sodium sulfate, filtered, evaporated under reduced pressure, and dried in vacuo to an orange-brown powder (440 mg). An analytical sample of the title compound can be isolated by preparative t.l.c. (20×20 cm SiO2 plate; eluent=9:1 chloroform:ethylacetate) with the bright-orange product eluting at the highest Rf (0.44), (50 mg from 200 mg applied). |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(O)=CC(O)=CC=C1;m1_m2:C1(CCC(=O)O1)=O, Reagents are:, and Products are 0:C(=O)(O)CC=C1C2=CC=C(C=C2OC=2C=C(C=CC12)O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Resorcinol (33.0 g, 0.300 mol) and succinic anhydride (30.0 g, 0.300 mol) were placed in a round bottomed flask and purged with nitrogen. Methanesulfonic acid (150 mL) was added and the solution was stirred at 65° C. for 2 hours under an atmosphere of nitrogen. The reaction mixture was added dropwise to rapidly stirred, ice-cooled water (1 L) with simultaneous addition of 50% aqueous sodium hydroxide to maintain pH 2.5 +/0.5. The product which appeared as a granular precipitate was collected by filtration and rinsed with water (3×100 mL) then acetone (3×100 mL). The product was air-dried then vacuum-dried (vacuum oven) at 110° C. for 18 hours to afford a dark red powder (37.7 g, 88%). |
Here is a chemical reaction formula: Reactants are:m2:P(O)(O)(O)=O;m1_m5:OC1=C(C=O)C=CC(=C1)O;m4:[H][H];m3:[H][H], Reagents are:m1_m5:CC(C)O;m6:[Pd], and Products are 0:CC1=C(C=C(O)C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2,4-Dihyroxybenzaldehyde (33.97 gm, 0.246 mol) (recrystallized from toluene) was dissolved in spectroscopic grade 2-propanol (3 L) in a round bottom flask fitted with a gas inlet and a bubbler outlet. 10% Palladium on carbon (1.35 gm) was added followed by phosphoric acid (3mL) and the mixture was sparaged with nitrogen. The nitrogen flow was switched to hydrogen and the mixture was rapidly stirred with ice cooling. After 3 hours hydrogen uptake was complete and the catalyst was removed by filtration. The filtrate was stripped down to 200 mL and 200 mL of ethyl acetate was added. The solution was washed with 4×200 mL of water and the combined water extracts back-extracted with ethyl acetate. These organic extracts were water washed and the combined organic layers dried over sodium sulfate and stripped down to afford the product as a colorless crystalline solid (29.95 gm, 98%). M.p.: 106° C. (Lit. 106°-107° C. [J. C. Bell, W. Bridge, and A. Robertson, J. Chem. Soc., 1542-45 (1937)]). NMR (DMSO-d6): δ 1.961 (s, Me), 6.076 (dd, H-6, J[5,6]=8 hz, J[2,6]=2 hz), 6.231 (d, H-2), 6.760 (d, H-5) 8.867 (s, OH), an 9.008 (s, OH). |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1=C(C=C(O)C=C1)O;m1_m2:C1(CCC(=O)O1)=O, Reagents are:, and Products are 0:C(=O)(O)CC=C1C2=CC(=C(C=C2OC=2C=C(C(=CC12)C)O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Methylresorcinol (25.8 g, 0.208 mol) and succinic anhydride (20.8 g, 0.208 g) were placed in a round bottom flask and the flask was purged with nitrogen. Methanesulfonic acid (150 mL) was added and the solution heated under nitrogen to 65° C. for 2 hours. The solution was added dropwise to 1 L of rapidly stirred, ice-cooled water with the simultaneous addition of 50% aq sodium hydroxide to maintain the pH at 2.25 +/-0.25. The product was collected by centrifugation and washed with water (3×) and acetone (2×). The solid was air-dried, then vacuum-dried at 110° C. to afford a brick-red powder (24.1 g, 74%). |
Here is a chemical reaction formula: Reactants are:m3:CC1=C(O)C=CC=C1O;m1_m2_m4:P(=O)(Cl)(Cl)Cl;m1_m2_m4:CN(C1=CC=CC=C1)C=O, Reagents are:m1_m2_m4:CCOCC, and Products are 0:OC1=C(C=O)C=CC(=C1C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Phosphorus oxychloride (80 mL, 0.86 mol) was added to a stirred mixture of N-methylformanilide (102 mL, 0.82 mol) in ether (250 mL). The mixture was stirred for 1 hour at room temperature and then cooled in ice. 2-Methyl resorcinol (Aldrich, 100 g, 0.81 mol) was added and the mixture was allowed to warm to room temperature while stirring overnight. The precipitated intermediate product was collected by filtration and rinsed with ether (3×). the intermediate was hydrolyzed by dissolving in a mixture of acetone (250 mL) and water (250 mL) and stirring for 30 minutes. Water (2 L) was added, the mixture was brought to a boil, and then allowed to cool and deposit crystalline product. This was recrystallized a second time from water (4 L) to afford pure product (70 g, 57%). M.p. 150° C. (Lit. 152°-3° C. [W. Baker et al., J. Chem. Soc., 2834-5 (1949). ]. NMR (DMSO-d6): δ 1.973 (s, 3H), 6.551 (d, J=8.5 hz, 1H), 7.428 (d, J-8.5 hz, 1H), 9.703 (s, 1H), 10.745 (s, 1H), and 11.592 (s, 1H). |
Here is a chemical reaction formula: Reactants are:m2_m3:P(O)(O)(O)=O;m1:OC1=C(C=O)C=CC(=C1C)O, Reagents are:m4:C(C)(C)O;m2_m3:[Pd], and Products are 0:CC1=C(O)C=CC(=C1O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2,4-dihydroxy-3-methylbenzaldehyde (30.0 g, 197 mmol) with isopropanol (3 L) was ice-cooled in a 5 L 3-neck flask fitted with a magnetic stirrer. Phosphoric acid (4 mL) and d10% palladium on carbon were added and the solution was sparged with nitrogen, then hydrogen. When uptake was judged to be complete (c. 1.5 hour) the solution was again sparged with nitrogen and then filtered through Celite®. The solvent was stripped off, the residue taken up in ethyl acetate, and the resulting solution washed with water (4×100 mL). The water washes were back-extracted with ethyl acetate and the combined organic layers dried over sodium sulfate and stripped down. Sublimation (95°, 0.05 torr) afforded a colorless solid (19.6 g, 72%). M.p. 107°-8° C. (Lit. 108°-109° C. [W. Baker et al., J. Chem. Soc., 2834-5 (1949).]). NMR (DMSO-d6): δ 1.969 (s, 3H), 2.037 (s, 3H), 6.220 (d, J=8.1 hz, 1H), 6.637 (d, J=8.1 hz, 1H), 7.929 (s, 1H), and 8.785 (s, 1H). |
Here is a chemical reaction formula: Reactants are:m2_m4:ICl;m1_m3:[C@@H]1(CC[C@@H](CO)O1)N1C(=O)NC(=O)C=C1, Reagents are:m2_m4:CO;m1_m3:CO, and Products are 0:IC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dideoxyuridine (2.122 g, 10.0 mmol) was dissolved in 30 mL of warm methanol and, after cooling to 25°, iodine monochloride (4.06 g, 25 mmol, 2.5 eq, Fisher) in methanol (20 mL) was added over 5 minutes. The dark purple reaction mixture was heated in a 50° bath under nitrogen for 20 minutes and then immediately cooled in an ice-water bath. After standing without stirring for 165 minutes, the resulting precipitate was collected by filtration and washed with cold methanol (2×10 mL). Vacuum-drying overnight afforded 2.232 g (66%) of iodide 21 as off-white microcrystals. This material was used without further purification in the next reaction, but other preparations were purified by chromatography or recrystallization from boiling methanol (30 mL/g) to give white needles (mp d 160°-164°). NMR indicated that the crude precipitate was homogeneous, but also that the 5'-hydroxyl proton was very broad due to exchange catalyzed by trace impurities. Chromatographed or recrystallized materials afforded spectra in which this proton was, as usual, a sharp triplet. |
Here is a chemical reaction formula: Reactants are:m3_m4:CO;m1_m2:I[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)NC(=O)C=C1;m1_m2:C(C#C)NC(C(F)(F)F)=O, Reagents are:m3_m4:ClCCl, and Products are 0:FC(C(=O)NCC#CC=1C(NC(N([C@H]2CC[C@@H](CO)O2)C1)=O)=O)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Iodouridine 21 was coupled for 3 hours to N-propargyltrifluoroacetamide following the general method given in Example 5C. Chromatography with a 0-5% methanol in dichloromethane gradient afforded material which was homogeneous by TLC, but which was difficult to dry. After co-evaporating the chromatographed product several times with chloroform and vacuum-drying, 536.5 mg of alkynylamino nucleoside 22 was obtained as a white foam. This material was homogeneous by TLC and was pure by NMR except for a small amount (39 mole%; corrected yield 66%) of chloroform. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC1=C(C=CC(=C1)F)O;m1_m2_m3_m4:C(C=C)C1=NOC(=N1)CCl;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m4:CC(=O)C, and Products are 0:C(C=C)C1=NOC(=N1)COC1=C(C=C(C=C1)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.71 g of 2-chloro-4-fluorophenol, 0.77 g of 3-allyl-5-chloromethyl-1,2,4-oxadiazole and 0.83 of potassium carbonate were added to 20 ml of acetone. After completion of the reaction, the resulting precipitates were filtered out from the mixture and then acetone was removed by distillation, and the residue was purified by column chromatography (benzene:hexane=1:1) to obtain 1.05 g of the desired product(yield: 80.8%). |
Here is a chemical reaction formula: Reactants are:m2:C(C)[Mg]Br;m3:Cl;m1_m4:C(C)OC(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl, Reagents are:m1_m4:O1CCCC1, and Products are 0:C(C)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.95 g of 3-ethoxycarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole was added to 30 ml of tetrahydrofuran. The mixture was cooled to -78° C., and then 3 ml of ethylmagnesium bromide (2M solution) was added dropwise. After the mixture was stirred at -78° C. for 1 hour, it was poured into cold aqueous 5% HCl solution. After the resulted product was extracted with ether and concentrated, it was purified by column chromatography(hexane:ethylacetate=4:1) to obtain 0.75 g of the desired product(yield: 83.0%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl;m1_m2_m3:Cl.ON, Reagents are:m1_m2_m3:CO, and Products are 0:ON=C(CC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.9 g of 3-ethylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.21 g of hydroxyamine hydrochloride were added to 10 ml of methanol. The mixture was heated to reflux for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(benzene:ether=1.1) to provide 0.80 g of the desired product(yield: 85.0%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(CC)C(=O)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl;m1_m2_m3:CC([O-])C.[Al+3].CC([O-])C.CC([O-])C, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:OC(CCC)C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.316 g of 3-propylcarbonyl-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole and 0.20 g of aluminum isopropoxide were added to 10 ml of isopropanol. The mixture was heated to reflux for 48 hours. After evaporation of isopropanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(hexane: ethylacetate=3:2) to provide 0.17 g of the desired product(yield: 54.0%). |
Here is a chemical reaction formula: Reactants are:m2:N;m1_m3:ClC(C1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl)(Cl)Cl;m1_m3:CO, Reagents are:, and Products are 0:N=COCC1=NOC(=N1)COC1=C(C=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.17 g of 3-(trichloromethyl)-5-[(2,4-dichlorophenoxy)methyl]-1,2,4-oxadiazole was added to 50 ml of methanol. An excess of ammonia gas was added with formation of bubble at 0° C. and then the mixture was stirred at room temperature for 4 hours. After evaporation of methanol, water was added to the residue. The aqueous solution was extracted with ethylacetate. After evaporation of ethylacetate, the residue was purified by column chromatography(hexane:ethylacetate) to provide 0.92 g of the desired product(yield: 50.9%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=O;m1_m2_m3_m4:Cl.ON;m1_m2_m3_m4:C(C)(=O)[O-].[K+], Reagents are:m1_m2_m3_m4:CO, and Products are 0:COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-formylbenzoate, 0.8 g of hydroxyamine hydrochloride, 1.1 g of potassium acetate and 10 ml of methanol were placed in a 50 ml eggplant type flask, and were stirred for 10 minutes at room temperature. Methanol was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The organic layer was washed with water, 5% hydrochloric acid and a saturated salt aqueous solution, and was dried with magnesium sulfate anhydride. After filtering, a small amount of Florisil was added to the resultant product, and was stirred for 5 minutes. The Florisil was filtered out, and ethyl acetate was distilled off under reduced pressure to obtain 1.5 g of the aimed compound (refractive index=1.5558) at a yield of 72%. |
Here is a chemical reaction formula: Reactants are:m1:COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NO;m2:BrC(C(=O)OCC)C, Reagents are:m4:CC(=O)C;m3:[Ag]=O, and Products are 0:COC1=NC(=NC(=C1)OC)OC1=C(C(=O)OC)C(=CC=C1)C=NOC(C)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.0 g of methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-hydroxyiminomethylbenzoate, 3 ml of ethyl 2-bromopropionate and 0.9 g of silver oxide (I) were place in a 50 ml eggplant type flask, and were allowed to stand for one night at room temperature. 10 ml of acetone and 10 g of silica gel were added to the resultant reaction liquor, and the acetone was distilled off under reduced pressure. The resultant product was purified by column chromatography to obtain 0.7 g of the aimed compound (refractive index=1.5261) at a yield of 27%. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)(=O)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC;m1_m2_m3_m4:Cl.C(C=C)ON;m1_m2_m3_m4:C(C)(=O)[O-].[K+];m1_m2_m3_m4:CO, Reagents are:m5:O, and Products are 0:C(C=C)ON=C(C)C1=C(C(=O)OC)C(=CC=C1)OC1=NC(=CC(=N1)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate, 1.0 g of allyloxyamine hydrochloride and 0.9 g of potassium acetate were added to 30 ml of methanol, and were refluxed with stirring for 5 hours. The reaction mixture was then poured into a cold water, and was extracted with ethyl acetate. The organic layer thus formed was washed with firstly dilute hydrochloric acid, then sodium hydrogencarbonate and water in sequence. The organic layer thus washed was then dried and concentrated. The residue oily product was purified by column chromatography to obtain 0.54 g of the aimed compound (melting point=76° to 78° C.) at a yield of 46% as a colorless transparent crystal. |
Here is a chemical reaction formula: Reactants are:m3:CC(C)(C#N)N=NC(C)(C)C#N;m2:C1CC(=O)N(C1=O)Br;m1:C1(=CC(=CC=C1)C(=O)OC)C, Reagents are:, and Products are 0:BrCC=1C=C(C(=O)OC)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methyl m-toluate was brominated with NBS and AIBN as described in Example 21 to give methyl m-bromomethylbenzoate, and this was further reacted with triethyl phosphite as described in Example 2 without further purification. |
Here is a chemical reaction formula: Reactants are:m2:C1CC(=O)N(C1=O)Br;m1:C1(=C(C=CC=C1)CC(=O)O)C;m3:CC(C)(C#N)N=NC(C)(C)C#N, Reagents are:, and Products are 0:BrCC1=C(C=CC=C1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: o-Tolylacetic acid was brominated with NBS and AIBN as described in Example 21 to give ethyl o-bromomethylphenylacetate, and this was reacted with triethyl phosphite as described in Example 2. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:NCCCCN1CCN(CC1)C1=NC=CC=N1;m0_m1_m2:C12C(OC(C(CC1)C2)=O)=O, Reagents are:, and Products are 0:N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared from 1.92 g (8.2 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl)piperazine and 1.14 g (8.14 mmol) of 3-oxabicyclo[3.2.1]octan-2,4-dione, substantially following the procedure of Example 1. Yield: 1.0 g (34% yield). |
Here is a chemical reaction formula: Reactants are:m2:C12C(OC(C(CCC1)C2)=O)=O;m1:NCCCCN1CCN(CC1)C1=NC=CC=N1, Reagents are:, and Products are 0:N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCCC(C1=O)C2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following substantially the procedure of Example 1, 2.78 g (11.8 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 1.88 g (12.2 mmol) of 3-oxabicyclo[3.3.1]nonan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (90:10), to give 2.04 g (47% yield) of the title compound. |
Here is a chemical reaction formula: Reactants are:m2:CC1(C2C(OC(C1CC2)=O)=O)C;m1:NCCCCN1CCN(CC1)C1=NC=CC=N1, Reagents are:, and Products are 0:N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)C2(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following substantially the procedure of Example 1, 0.54 g (2.34 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 0.36 g (2.14 mmol) of 8,8-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4), to give 0.25 g (32% yield) of the title compound. |
Here is a chemical reaction formula: Reactants are:m2:CC12C(OC(C(CC1)(C2)C)=O)=O;m1:NCCCCN1CCN(CC1)C1=NC=CC=N1, Reagents are:, and Products are 0:N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2(CCC(C1=O)(C2)C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following substantially the procedure of Example 1, 4.2 g (17.8 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine was reacted with 2.99 g (17.8 mmol) of 1,5-dimethyl-3-oxabicyclo[3.2.1]octan-2,4-dione. The product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4), to give 1.4 g (21% yield) of the title compound. |
Here is a chemical reaction formula: Reactants are:m4:C12C(OC(C(CC1)CC2)=O)=O;m3:C12C(OC(C(CC1)CC2)=O)=O;m1_m2:NCCCCN1CCN(CC1)C1=NC=CC=N1;m1_m2:C12C(OC(C(CC1)CC2)=O)=O, Reagents are:, and Products are 0:N1=C(N=CC=C1)N1CCN(CC1)CCCCN1C(C2CCC(C1=O)CC2)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: An intimate mixture of 0.5 g (2.14 mmol) of 1-(4-aminobutyl)-4-(2-pyrimidinyl) piperazine and 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was heated in an oil bath at 220°-230° C. for 15 minutes. An additional 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]nonan-2,4-dione was added. Heating in an oil bath at 220°-230° C. was continued for 15 minutes and then an additional 0.22 g (1.42 mmol) of 3-oxabicyclo[3.2.2]-nonan-2,4-dione was added. Heating was continued for 30 minutes at 220°-230° C. and then the reaction mixture was cooled. The resulting product was chromatographed on silica gel, eluting with dichloromethane/methanol (96:4 followed by 94:6), to give 46 mg of the title compound (6% yield). |
Here is a chemical reaction formula: Reactants are:m1_m2:[C@H]1(CC[C@@H](CC1)C(=O)O)C(=O)O, Reagents are:m1_m2:C(C)(=O)OC(C)=O, and Products are 0:C12C(OC(C(CC1)CC2)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2.9 g of cis-cyclohexane-1,4-dicarboxylic acid in 25 ml of acetic anhydride was heated under reflux for 2.5 hours. The solvent was removed by evaporation in vacuo, and the residue was triturated under diethyl ether several times. The residue was dried under high vacuum to give 2.5 g (97% yield) of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:[C@H]1(C[C@@H](CC1)C(=O)O)C(=O)O, Reagents are:m1_m2:C(C)(=O)OC(C)=O, and Products are 0:C12C(OC(C(CC1)C2)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.63 g of cis-cyclopentane-1,3-dicarboxylic acid in 8.2 ml of acetic anhydride was heated in an oil bath at ca. 100° C. for 45 minutes. The excess acetic anhydride and acetic acid were removed by evaporation in vacuo to give a solid which was triturated under diethyl ether. This afforded 1.14 g (79% yield) of the title anhydride. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m4_m3:C(C)O;m1_m5_m2_m4_m3:C(C)(=O)N1CCC2=CC(=CC(=C12)[N+](=O)[O-])Br;m1_m5_m2_m4_m3:Cl, Reagents are:m1_m5_m2_m4_m3:[Fe];m1_m5_m2_m4_m3:O, and Products are 0:C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixed solution of ethanol (400 ml) and water (100 ml), were added N-acetyl-5-bromo-7-nitroindoline (133.1 g), iron powder (10 mesh; 75 g) and concentrated hydrochloric acid (5 ml), and the mixture was subjected to refluxing for 5 hours with vigorous stirring. The reaction mixture was filtered by suction while hot to remove insoluble matter, and then the filtrate thereof was concentrated and cooled on standing to give the intended compound 38.3 g (32.2%) as a brown needle crystal. M.P.: 154°-155° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)N1CCC2=CC(=CC(=C12)N)Br;m6_m5:[C-]#N.[Na+];m3:N(=O)[O-].[Na+];m4:C([O-])([O-])=O.[Na+].[Na+];m1:Cl, Reagents are:m6_m5:[Cu](C#N)C#N, and Products are 0:C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into 6N hydrochloric acid (178.5 ml) was suspended N-acetyl-7-amino-5-bromoindoline (51.0 g), and aqueous solution (212 ml) of sodium nitrite (21.2 g) was dropwise added thereto under cooling with stirring over 30 minutes and at the inside temperature of not higher than -1° C. After stirred for 30 minutes at the temperature as such, sodium carbonate was added to the reaction mixture to neutralize it. This reaction mixture was poured into aqueous solution (200 ml) of copper cyanide (27.5 g) and sodium cyanide (30.7 g), and the mixture was allowed to stand for one night at room temperature. The reaction mixture was again subjected to stirring for 30 minutes at the inside temperature of 50° C. and was cooled to give a deposited crystal, which was then collected by filtration, washed with water and dried. The crude crystal was recrystallized from acetonitrile to give the intended compound 43.0 g (81.1%). M.P.: 170°-175° C. |
Here is a chemical reaction formula: Reactants are:m3:[OH-].[Na+];m4:O;m1_m2:Cl;m1_m2:C(C)(=O)N1CCC2=CC(=CC(=C12)C#N)[N+](=O)[O-], Reagents are:, and Products are 0:[N+](=O)([O-])C=1C=C2CCNC2=C(C1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into concentrated hydrochloric acid (63.6 ml) was dissolved N-acetyl-7-cyano-5-nitroindoline (5.3 g), which was then subjected to stirring at 140° C. for 45 minutes. The reaction mixture was cooled to 0° C. to give deposited crystal, which was then collected by filtration. The obtained crude crystal was suspended into water (50 ml), and was rendered basic by adding 50% sodium hydroxide, and the insoluble matter was collected by filtration. After adding concentrated hydrochloric acid to the filtrate, the deposited crystal was collected by filtration and dried to give the intended compound 3.7 g (77.1%) as yellow powder. M.P.: 294°-297° C. (decomp.) |
Here is a chemical reaction formula: Reactants are:m1_m4:BrC=1C=C(C2=C(CCCCN2)C1)C(=O)O;m2_m3:C([O-])([O-])=O.[K+].[K+];m2_m3:C(C1=CC=CC=C1)Br, Reagents are:m1_m4:CN(C)C=O, and Products are 0:C(C1=CC=CC=C1)OC(=O)C1=CC(=CC=2CCCCNC21)Br, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 7-bromo-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid (8.53 g) dissolved in DMF (80 ml), were added potassium carbonate (13.8 g) and benzyl bromide (4.5 ml) and the mixture was stirred for 2 hours at room temperature. After the insoluble matter was filtered off and the filtrate was concentrated, a mixed liquid of ethyl acetate-benzene (1:1, 400 ml) was added to the residue, and the mixture was washed with water, dried over anhydrous sodium sulfate and then subjected to distilling off the solvent to give the intended compound 11.35 g (99.7%) as brown oily matter. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)OC(=O)C1=CC(=CC=2CCCCNC21)C#N;m1_m2_m3:[OH-].[Na+];m1_m2_m3:O.C(C)O;m4:Cl, Reagents are:m5:O, and Products are 0:N1CCCCC2=C1C(=CC(=C2)C(=O)O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7-Cyano-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid benzyl ester (3.30 g) and sodium hydroxide (2 g) in a mixed solution of water-ethanol (1:1, 60 ml) was refluxed for 8 hours. After cooled, water (100 ml) was added to the reaction mixture, which was then rendered to have pH 3 with concentrated hydrochloric acid. The deposited crystal was collected by filtration, washed with water and dried to give the intended compound 1.84 g (85.0%), which was then recrystallized from ethanol to give slightly yellow crystal. M.P.: 287°-288° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:C([O-])([O-])=O.[K+].[K+];m2_m3:CI;m1_m4:[N+](=O)([O-])C=1C=C(C2=C(CCCCN2)C1)C(=O)O, Reagents are:m1_m4:CN(C)C=O, and Products are 0:COC(=O)C1=CC(=CC=2CCCCNC21)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7-Nitro-2,3,4,5-tetrahydro-1H-1-benzazepine-9-carboxylic acid (6.25 g) was dissolved into DMF (50 ml), to which then potassium carbonate (11 g) and methyl iodide (4.9 ml) were added, and was stirred for 2 hours at room temperature. After the insoluble matter was filtered off and the filtrate was concentrated, ethyl acetate (500 ml) was added to the residue, which was then washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to give the intended compound 6.65 g (quantitatively) as yellow crystal. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC=1N=NC(=CC1)CC;m1_m2_m3_m4:N1CCC(C(=O)OCC)CC1;m1_m2_m3_m4:C(C)(C)N(CC)C(C)C;m1_m2_m3_m4:CN1CCCC1, Reagents are:m5:O, and Products are 0:C(C)C1=CC=C(N=N1)N1CCC(CC1)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.67 g (0.011 mol) of 3-bromo-6-ethylpyridazine was added to 1.5 mL (10 mmol) ethyl isonipecotate and 3.5 mL (20 mmol) diisopropylethylamine and 5 mL N methylpyrrolidine (NMP). This mixture was heated to 140° C. for 4 hours. Upon cooling 100 mL of water was added to the mixture and the contents were extracted with methylene chloride then washed twice with water and once with brine and the solvent evaporated in vacuo. The resulting oil was eluted through a short silica gel plug with 80% ethyl acetate and 20% hexanes and dried in vacuo. This intermediate was taken up in 25 mL THF and was exposed to 3-fold excess lithium aluminum hydride with stirring under nitrogen for 1 hour. The reaction was chilled on ice and quenched by dropwise addition of water. The slurry was dried, treated with charcoal and filtered yielding 6-ethyl-3-(4-hydroxymethyl-1-piperidinyl)pyridazine (Formula IV: R1 =C2H5 ; Y=CH2 ). |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m3_m5:C(#N)C1=CC=C(C=C1)O;m1_m2_m3_m5:C(C1=CC=CC=C1)Cl;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m5:CN1CCCC1=O, and Products are 0:C(C1=CC=CC=C1)OC1=CC=C(C#N)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture containing 325 g of 4-cyanophenol, 346 mL of benzyl chloride and 758 g of potassium carbonate in 1.2 L of NMP was heated at 95° C. with stirring for 1.5 hrs. The reaction mixture was cooled to room temperature and poured into 5 L of cold water. The resulting white solid was collected, washed with water and hexanes and dried at 70° C. in vacuo giving 570.0 g of 4-benzyloxybenzonitrile. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m3_m5:C(C1=CC=CC=C1)OC1=CC=C(C#N)C=C1;m1_m2_m3_m5:Cl.C(C)N(CC)CC;m1_m2_m3_m5:[N-]=[N+]=[N-].[Na+], Reagents are:m1_m2_m3_m5:CN(C)C=O;m6:O, and Products are 0:C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=NN=NN1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 285 g of the nitrile, 262.5 g triethylamine hydrochloride and 124 g of sodium azide in 1.5 L of DMF under nitrogen was stirred under reflux for 18 hrs. The reaction mixture was cooled to room temperature, poured into 4 L of cold water and acidified with 3N HCl. The resulting white solid was collected, washed with water and dried at 60° C. in vacuo for 48 hrs to give 337 g of 5-(4-benzyloxyphenyl)tetrazole. |
Here is a chemical reaction formula: Reactants are:m3_m5:CI;m1_m2_m4:C(C1=CC=CC=C1)OC1=CC=C(C=C1)C1=NN=NN1;m1_m2_m4:CCN(C(C)C)C(C)C, Reagents are:m3_m5:CN1CCCC1=O;m7:O;m1_m2_m4:CN1CCCC1=O;m6:O, and Products are 0:CN1N=C(N=N1)C1=CC=C(C=C1)OCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution containing 337 g of the tetrazole and 362 mL of DIPEA in 1 L of NMP cooled to 18° C. under N2 was added dropwise over 1.5 hrs 200 g of methyl iodide in 170 mL NMP. After stirring an additional hour at room temperature, the reaction mixture was diluted with 340 mL of water and the reaction mixture was diluted with 340 mL of water and cooled to 18° C. The resulting solid was collected, washed with water, recrystallized from ethanol and dried in vacuo at 50° C. to give 232.3 g of 2-methyl-5-(4-benzyloxyphenyl)-2H-tetrazole. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1=CC=C(N=N1)Cl;m1_m2_m3_m4:N1CCC(C(=O)OCC)CC1, Reagents are:m1_m2_m3_m4:CN1CCCC1=O;m1_m2_m3_m4:C(C)(C)N(CC)C(C)C, and Products are 0:C(=O)(OCC)C1CCN(CC1)C=1N=NC(=CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 55 mmoles of 6-methyl-3-chloropyridazine was added to 75 mmoles of ethyl isonipecotate in 5 mL NMP and 20 mL diisopropylethylamine (DIPEA) and refluxed for 6 hours. The product was isolated as described in Example 1a above to give a 44% yield of 3-(4-carboethoxy-1-piperidinyl)-6-methylpyridazine. Reduction of 18.8 mmol of this compound using 56.6 mmol DIBAL in 100 mL THF with a Rochelle's salt quench gave 3-(4-hydroxymethyl-1-piperidinyl)-6-methylpyridazine (Formula IV: R1 =CH3 ; Y=CH2) which was used unpurified in the final step. Reaction of 5 mmol of the product described in Example 1b with 4.5 mmol of the 3-(4-hydroxymethyl-1-piperidinyl)-6-methyl pyridazine according to the procedure of Example 1c afforded after recrystallization from ethyl acetate at -70° C. the compound of formula I (R1 =R4 =CH3, Y=CH 2, R2 =R3 =hydrogen) in 12% yield, m.p. 180°-185° C. |
Here is a chemical reaction formula: Reactants are:m3:OC1CCNCC1;m2:CCN(C(C)C)C(C)C;m1:CC1=CC=C(N=N1)Br, Reagents are:, and Products are 0:C(CC)C1=CC=C(N=N1)N1CCC(CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following a procedure similar to that of Example 3, 81 millimoles of 6-methyl-3-bromopyridazine was combined with 16 mL DIPEA and 163 mmoles of 4-hydroxypiperidine and heated to 120° for 16 hours to obtain 6-methyl-3-(4-hydroxy-1-piperdinyl)pyridazine (Formula IV: Y=bond, R=CH3) in 24% yield. 6.8 Mmols of the latter and 7.4 mmoles of 2-methyl-5-(4-hydroxy-3,5-dimethyl phenyl)-2H-tetrazole (Formula III: R2 =R3 =R4 =CH3) were reacted with equimolar amounts of DEAD and TPP essentially as described above in Example 1c. Recrystallization from methanol gave a 74% yield of the compound of Formula I (R1 =R2 =R3 =R4 =CH3, Y=bond), m.p. 188°-189° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m4:N1=CC=C(C=C1)CC(=O)OCC;m1_m2_m5_m3_m4:Cl, Reagents are:m1_m2_m5_m3_m4:C(C)O;m1_m2_m5_m3_m4:[H][H];m1_m2_m5_m3_m4:[Pt]=O, and Products are 0:N1CCC(CC1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.5 g (0.1 mol) Ethyl 4-pyridylacetate, 8.4 mL (0.1 mol) 12N hydrochloric acid and 2.5 g platinum oxide were dissolved in absolute ethanol and hydrogenated at 40 psi hydrogen on a Parr shaker. After 1 hour, the contents of the vessel were filtered and concentrated in vacuo yielding 27.79 g of ethyl 4-piperidinylacetate. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(=O)O;m4:C(#N)[BH3-].[Na+];m1:ClC=1C=C(C=CC1)NCCN;m2:Cl.N12CC(C(CC1)CC2)=O, Reagents are:m5:CO, and Products are 0:N12CC(C(CC1)CC2)NCCNC2=CC(=CC=C2)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of N-(3-chlorophenyl)-1,2-diaminoethane (1 g; 0,00586 moles) in 25 ml of anhydrous methanol kept under nitrogen atmosphere, 3-quinuclidinone hydrochloride (1.01 g, 0.0062? moles) is added. The pH is adjusted to pH 6 by addition of glacial acetic acid. Sodium cyanoborohydride (0.74 g; 0.0117 moles) is added in two portions. The reaction mixture is refluxed for 10 hours, cooled and then filtered. After evaporation to dryness the residue is taken up with water, basified with 20% sodium hydroxide solution and extracted three times with ethyl acetate. The organic layer is washed with brine, dried over anhydrous sodium sulfate and, after filtration, evaporated to dryness. The residue is purified by silica gel flash-chromatography (methylene chloride--methanol--30% ammonium hydroxide, 150:50:5 as eluant) to give the desired product as a clear oil (0.06 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrCCCCN1C=NC2=C1C=CC=C2;m1_m2_m3:N1(CCNCC1)C1=CC2=C(OCCO2)C=C1, Reagents are:m1_m2_m3:C(C)#N, and Products are 0:N1(C=NC2=C1C=CC=C2)CCCCN2CCN(CC2)C2=CC1=C(OCCO1)C=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogously to Example 1, reaction of 1-(4-bromobutyl)benzimidazole with 6-piperazino-1,4-benzodioxane ("A") in 200 ml of acetonitrile gives 6-[4-(4-(benzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane, m.p. 247-248°. |
Here is a chemical reaction formula: Reactants are:m3_m4:NCCCCC1=CNC2=CC=C(C=C12)C(=O)OCC;m3_m4:C(C)OC(=O)C=1C=C2C=CNC2=CC1;m5:ClCCCC(=O)Cl, Reagents are:m0_m1_m2_m6_m7:CC(=O)C;m0_m1_m2_m6_m7:O, and Products are 0:ClCCCCC1=CNC2=CC=C(C=C12)C(=O)OCC;0:C1(C=2C(C(N1CCCCC1=CNC3=CC=C(C=C13)C(=O)OCC)=O)=CC=CC2)=O;0:O1CCOC2=C1C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2.18 g of 3-(4-aminobutyl)-5-ethoxycarbonylindole [obtainable from 5-ethoxycarbonylindole by reaction with 4-chlorobutyryl chloride, reduction of the product to give 3-(4-chlorobutyl)-5-ethoxycarbonylindole and conversion into 3(4-phthalimidobutyl)-5-ethoxycarbonylindole] and one equivalent of 6-N,N-bis(2-chloroethyl)amino)-1,4-benzodioxane ("B") in 40 ml of acetone and 40 ml of water is boiled for 24 hours and worked up in the conventional manner. 6-[4-(4-(5-ethoxycarbonylindol-3-yl)butyl)piperazino]-1,4-benzodioxane is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:NCCCCN1C=NC2=C1C=CC(=C2)C(=O)OCC;m1_m2:ClCCN(CCCl)C1=CC2=C(OCCO2)C=C1, Reagents are:, and Products are 0:C(C)OC(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogously to Example 3, reaction of 1-(4-aminobutyl)-5-ethoxycarbonylbenzimidazole with 6-(N,N-bis(2-chloroethyl)amino)-1,4-benzodioxane ("B") gives 6-[4(4-(5-ethoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:[N+](=O)([O-])C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1;m1_m3_m2_m4:C(C)(=O)Cl, Reagents are:m1_m3_m2_m4:C1CCOC1;m1_m3_m2_m4:C1CCOC1, and Products are 0:C(C)(=O)NC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4.21 g of 6-[4-(4-(5-aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane ("C") [obtainable as in Example 5] in 35 ml of THF is treated with a solution of 0.9 g of acetyl chloride in 10 ml of THF, and the mixture is stirred at 50° for 2 hours, evaporated and worked up in the conventional manner. 6-[4-(4-(5-Acetamidoindol-3-yl)butyl)piperazino]-1,4-benzodioxane is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:NC=1C=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C1;m1_m2:C(C)(=O)Cl, Reagents are:, and Products are 0:C(C)(=O)NC=1C=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogously to Example 6, reaction of 6-[4-(4-(6-aminobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane ("D") with acetyl chloride gives 6-[4-(4-(6-acetamidobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2:NC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1;m1_m2:C(C)(=O)Cl, Reagents are:, and Products are 0:C(C)(=O)NC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogously to Example 7, reaction of 6-[4-(4-(5-aminobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane ("E") with acetyl chloride gives 6-[4-(4-(5-acetamidobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1, Reagents are:m1_m2:CO;m3:[Pd], and Products are 0:NC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 3.8 g of 6-[4-(4-(5-nitroindol-3-yl)butyl)piperazino]-1,4-benzodioxane in 45 ml of methanol is hydrogenated with stirring on 0.1% Pd-C at 20° and 1 bar until absorption of H2 is complete. The mixture is poured into ice-water, worked up in the conventional manner and gives 6-[4-(4-(5-aminoindol-3-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(#N)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1;m1_m2_m4_m3:[OH-].[Na+];m1_m2_m4_m3:C(C)OCCOCCO, Reagents are:m1_m2_m4_m3:O, and Products are 0:C(N)(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.16 g of 6-[4-(4-(5-cyanobenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane, 2.4 g of NaOH, 50 ml of H2O and 40 ml of diethylene glycol monoethyl ether is stirred at a bath temperature of 140° for 3 hours. The mixture is then cooled to room temperature, worked up in the conventional manner and gives 6-[4-(4-(5-carbamoylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m4:[OH-].[Na+];m1_m5:COC(=O)C1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1;m2_m3_m6:N#N;m2_m3_m6:[H-].[Al+3].[Li+].[H-].[H-].[H-], Reagents are:m1_m5:C1CCOC1;m2_m3_m6:C1CCOC1, and Products are 0:OCC1=CC2=C(N(C=N2)CCCCN2CCN(CC2)C2=CC3=C(OCCO3)C=C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4.4 g of 6-[4-(4-(5-methoxycarbonylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane in 40 ml of THF is added dropwise with stirring in an N2 atmosphere at 20° to a suspension of 0.6 g of lithium aluminium hydride in 20 ml of THF. The mixture is stirred at 20° for 1 hour, decomposed with dilute sodium hydroxide solution and filtered, and the filtrate is worked up in the conventional manner and gives 6-[4-(4-(5-hydroxymethylbenzimidazol-1-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(=CC=CC=C1)S(=O)(=O)N1C=C(C2=CC(=CC=C12)Br)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1;m1_m2_m3:[OH-].[K+], Reagents are:m1_m2_m3:C(C)O, and Products are 0:BrC=1C=C2C(=CNC2=CC1)CCCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.7 g of 6-[4-(4-(1-benzenesulfonyl-5-bromoindol-3-yl)butyl)piperazino]-1,4-benzodioxane is boiled for 16 hours with 1.5 g of KOH in aqueous ethanol solution, worked up in the conventional manner and gives 6-[4-(4-(5-bromoindol-3-yl)butyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(#N)C=1C=C2C(=CNC2=CC1)CCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1;m1_m2_m4_m3:[OH-].[Na+];m1_m2_m4_m3:C(C)OCCOCCO, Reagents are:m1_m2_m4_m3:O, and Products are 0:C(N)(=O)C=1C=C2C(=CNC2=CC1)CCCN1CCN(CC1)C1=CC2=C(OCCO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3.1 g of 6-[4-(3-(5-cyanoindol-3-yl)propyl)piperazino]-1,4-benzodioxane, 2.7 g of NaOH, 100 ml of water and 50 ml of diethylene glycol monoethyl ether is stirred at a bath temperature of 140° for 3 hours. It is cooled, worked up in the conventional manner and gives 6-[4-(3-(5-carbamoylindol-3-yl)propyl)piperazino]-1,4-benzodioxane. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)NC(OCC)=O;m1_m2:Br, Reagents are:, and Products are 0:Br.C1(=CC=CC2=CC=CC=C12)C1CCNCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 10.5 g of the compound obtained in Stage A in 300 ml of a 48% hydrobromic acid solution, are refluxed for 20 hours. After evaporation and washing twice with ethanol, the residue is taken up in acetone and the mixture then filtered to give 4-(naphth-1-yl)piperidine hydrobromide. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m3_m5:Br.C1(=CC=CC2=CC=CC=C12)C1CCNCC1;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m5:BrCC#N, Reagents are:m1_m2_m3_m5:CC(=O)C, and Products are 0:Cl.C1(=CC=CC2=CC=CC=C12)C1CCN(CC1)CC#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5 g of the compound from Example 3, 7.088 g of potassium carbonate and 2.259 g of bromoacetonitrile in 200 ml of acetone are stirred for 10 hours under reflux and a stream of nitrogen. After filtering and evaporation of the filtrate, the residue obtained is treated with an ethanolic solution of hydrogen chloride to give 4.5 g of the expected hydrochloride. |
Here is a chemical reaction formula: Reactants are:m1_m3:C(=C)C=1C=C(CO)C=CC1;m1_m3:C(Cl)(Cl)(Cl)Cl;m2:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:, and Products are 0:C(=C)C=1C=C(CCl)C=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3-Ethenylbenzyl alcohol (5.26 g) was dissolved in carbon tetrachloride (100 ml) and triphenylphosphine (10.2 g) added. The solution was refluxed overnight and then left to cool. A white precipitate formed which was filtered through celite. The filtrate was evaporated in vacuo to yield a crude product. The residue was purified by gravity chromatography on silica using 5% dichloromethane in petrol (60-80) as eluant. This yielded the pure product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:Cl.N12CC(C(CC1)C2)=O;m1_m2_m4:C(C1=CC=CC=C1)(=O)C1=CC=CC=C1;m3:C[Si](C)(C)[N-][Si](C)(C)C.[Li+], Reagents are:m1_m2_m4:C1CCOC1, and Products are 0:C1(=CC=CC=C1)C(C1N2CCC(C1=O)C2)(O)C2=CC=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of 1-azabicyclo[2.2.1]heptan-3-one hydrochloride (1.06 g) and benzophenone (1.82 g) in dry THF (5 ml) at -78° C. under argon was added a solution of lithium bis(trimethylsilyl)amide (18 ml, 1.0M in THF). The solution was stirred at -78° C. for 1 h, allowed to warm to room temperature and stirred for 48 h. The mixture was poured onto water and extracted with dichloromethane (×4). The combined extracts were dried (Na2SO4), evaporated in vacuo, and the residue was purified by chromatography on silica using a gradient elution of 10-30% ethyl acetate in dichloromethane to afford the title compound as a white solid: |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:ClC1=C(C=O)C=CC=C1;m2_m3_m4:[OH-].[K+];m1:N12CC(C(CC1)CC2)=O, Reagents are:m2_m3_m4:CO, and Products are 0:ClC1=C(C=C2N3CCC(C2=O)CC3)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Azabicyclo[2.2.2]octan-3-one (3.86 g) was heated at reflux with 2-chlorobenzaldehyde (8.33 ml), potassium hydroxide (0.4 g) and methanol (60 ml) under nitrogen for 2.5 hours. The volatiles were removed in vacuo and the residue washed with sodium hydrogen carbonate. This was extracted (×4) with dichloromethane. The organic layer was washed with water and dried (MgSO4). The dichloromethane was removed in vacuo and the residue recrystallised from methanol-dichloromethane, to afford the title compound as yellow crystals: |
Here is a chemical reaction formula: Reactants are:m5:C(C)N(CC)CC;m1_m6:N([C@H](CC1=CC=CC=C1)C(=O)O)C(=O)OC(C)(C)C;m3:ClC(=O)OCC(C)C;m4_m7:N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1.Cl;m2:CN1CCOCC1, Reagents are:m1_m6:C1CCOC1;m4_m7:C(Cl)(Cl)Cl, and Products are 0:N([C@H](CC1=CC=CC=C1)C(=O)N1[C@H](C(=O)OCC2=CC=CC=C2)CCC1)C(=O)OC(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Boc-(D)Phe-Pro-OH was produced by first preparing the dipeptide benzyl ester and then removing the ester by catalytic hydrogenation. Boc-(D)Phe-OH (10.0 g, 37.7 mmoles) was dissolved in 50 mL of THF and N-methylmorpholine (4.14 mL, 37.7 mmoles) was added. The solution was cooled to -20° and isobutyl chloroformate (4.90 mL, 37.7 mmoles) was added. After 5 min, H-Pro-OBzl.HCl (9.11 g, 37.7 mmoles), dissolved in 50 mL of chloroform and cooled to -20°, was added. Triethylamine (5.25 mL, 37.7 mmoles) was added and the mixture was stirred for 1 h at -20° and 2 h at room temperature. The reaction mixture was filtered and the filtrate evaporated. The residue was dissolved in ethyl acetate and was washed with 0.2N hydrochloric acid, 5% aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated to yield 15.2 g of Boc-(D)Phe-Pro-OBzl as an oil. The benzyl ester (15.2 g) was dissolved in 100 mL of methanol and it was hydrogenated at an initial pressure of 40 psi on a Parr apparatus in the presence of 0.5 g of 10% Pd/C. The reaction solution was filtered through Celite™ and evaporated to yield a solid. This solid material was isolated and was washed with ethyl acetate and then by ether to yield 10.0 g of the desired product (mp 176.5°-177°). |
Here is a chemical reaction formula: Reactants are:m5:Cl;m2:FC(C(=O)O)(F)F;m1:N(CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1)C(=O)OC(C)(C)C;m3_m4:N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1;m3_m4:FC(C(=O)[O-])(F)F, Reagents are:m6:CCOCC;m7:C(C)(=O)OCC, and Products are 0:NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)OCC1=CC=CC=C1.Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparation of H-Leu-Ala-OBzl except that the trifluoroacetate salt was soluble in ether. The preparation was dissolved in ethyl acetate and treated with anhydrous hydrogen chloride. The resulting product was precipitated by the addition of ether to yield 7.7 g of H-Gly-Leu-Ala-OBzl HCl in a first crop. |
Here is a chemical reaction formula: Reactants are:m3:C(Cl)C1CO1;m1_m2:ClC=1C=C(C=CC1)N1CCNCC1;m1_m2:[H-].[Na+], Reagents are:, and Products are 0:ClC=1C=C(C=CC1)N1CCN(CC1)CC1CO1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 1.50 g of 4-(3-chlorophenyl)-piperazine and 0.31 g of sodium hydride was added 2.4 ml of epichlorohydrin and the reaction mixture as stirred at room temperature for 30 minutes. After the reaction was completed, the reaction mixture was extracted with 100 ml of ethyl acetate, and the extract was washed 5 times with 100 ml of water, then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain the residue which was purified by means of a silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:1) to obtain 1.66 g of 4-(3-chlorophenyl)-1-(2,3-epoxypropyl)piperazine as in the form of an oily substance. |
Here is a chemical reaction formula: Reactants are:m1_m3:CC1=CC(=C(C(=C1)C)O)C(CC1=CC=CC=C1)=O;m2:C(C)(=O)OC(C)=O, Reagents are:m1_m3:CN(C)CN(C)C, and Products are 0:CC1=C(C(=CC(=C1)C)C(C(=C)C1=CC=CC=C1)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 212.6 Grams of 4,6-dimethyl-2-(2-phenylacetyl)-phenol was dissolved in 350 ml of N,N,N',N'-tetramethyldiaminomethane, then under ice-cooled condition with stirring, 350 ml of acetic anhydride was added dropwise thereto. The reaction mixture was further stirred at room temperature for 2 hours, then was poured in 1 kg of ice and stirred vigorously. The crystals separated in the mixture were collected by filtration, washes with water, then dried. Recrystallized from ethanol to obtain 186 g of 2,4-dimethyl-6-(2-phenylacryloyl)phenol. Colorless needle-like crystals. Melting point: 83°-84° C. |
Here is a chemical reaction formula: Reactants are:m1:S(O)(O)(=O)=O;m2:CC1=C(C(=CC(=C1)C)C(C(=C)C1=CC=CC=C1)=O)O, Reagents are:, and Products are 0:CC1=C2CC(C(C2=C(C(=C1)C)O)=O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into 15 ml of concentrated sulfuric acid, under ice-cooled condition with stirring, 3.0 g of 2,4-dimethyl-6-(2-phenylacryloyl)phenol was added gradually, then the whole mixture was stirred at room temperature for 1 hour. The reaction mixture was poured in 100 g of ice and extracted with 200 ml of methylene chloride. The extract was washed with water and dried with anhydrous magnesium sulfate, then was concentrated under a reduced pressure to obtain the residue. The residue was recrystallized from ethanol to obtain 2.11 g of 2,3-dihydro-4,6-dimethyl-2-phenyl-7-hydroxy-1H-inden-1-one. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m3:[OH-].[Na+];m1_m2_m5:COC1=C(C=C(C=C1)C)C(CC)=O;m1_m2_m5:C(C1=CC=CC=C1)=O, Reagents are:m1_m2_m5:C(C)O, and Products are 0:COC1=C(C=C(C=C1)C)C(C(C)=CC1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 140 g of 2'-methoxy-5'-methylpropiophenone, 83.4 g of benzaldehyde and 1.5 liters of ethanol was added 154 ml of 20%-sodium hydroxide aqueous solution under stirring. The reaction mixture was stirred overnight at room temperature, then 10%-hydrochloric acid was added to make the reaction mixture acidic, and extracted with benzene. The benzene extract was washed with water and an aqueous solution saturated with sodium chloride in this order, then dried to obtain 212 g of 2'-methoxy-5'-methyl-2-benzylidenepropiophenone. Yellow oily substance. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1C(C2=C(C=CC(=C2C1C1=CC=CC=C1)C)O)=O;m1_m2_m3_m4:C(C=CC)Br;m1_m2_m3_m4:[OH-].[K+], Reagents are:m1_m2_m3_m4:CC(=O)C, and Products are 0:CC1C(C2=C(C=CC(=C2C1C1=CC=CC=C1)C)OCC=CC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 19.0 g of 2,3-dihydro-2,4-dimethyl-3-phenyl-7-hydroxy-1H-inden-1-one, 13.98 of crotyl bromide and 5.47 g of potassium hydroxide in 200 ml of acetone was heated and refluxed under stirring condition. After the reaction was completed, the reaction mixture was concentrated and extracted with ethyl acetate, then the extract was washed with water and with an aqueous solution saturated with sodium chloride, then dried. The extract was concentrated by removing the solvent under a reduced pressure, then recrystallized from methanol to obtain 11.8 g of 2,3-dihydro-2,4-dimethyl-3-phenyl-7-crotyloxy-1H-inden-1-one as in the form of cis-trans mixture. Colorless stick-like crystals. Melting point: 138.5°-139.5° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1C(C2=C(C=CC(C2C1C1=CC=CC=C1)(C)C)OCC=CC)=O;m1_m2:C1CCCC2=CC=CC=C12, Reagents are:, and Products are 0:CC1C(C2=C(C(=CC(=C2C1C1=CC=CC=C1)C)C(C=C)C)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 11 Grams of 2,3-dihydro-2,4-dimethyl-3-phenyl-4-methyl-7-crotyloxy-1H-inden-1-one was added to 55 ml of tetrahydronaphthalene and the mixture was heated and refluxed for 6 hours with stirring condition. After the reaction was completed, the reaction mixture was concentrated by removal of the solvent, and the residue thus obtained was purified by means of a silica gel column chromatography. 11.2 Grams of 2,3-dihydro-2, 4-dimethyl-3-phenyl-6-(1-buten-3-yl)-7-hydroxy-1H-inden-1-one was obtained as cis-trans mixture. Yellow oily substance. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:CC1=C2CC(C(C2=C(C(=C1)C)O)=O)=CC1=CC=C(C=C1)OC;m2_m5:[H][H], Reagents are:m1_m3_m4:C(C)OC(C)=O;m1_m3_m4:C(C)(=O)O;m2_m5:[Pd], and Products are 0:CC1=C2CC(C(C2=C(C(=C1)C)O)=O)CC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.09 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-(4-methoxybenzylidene)-1H-inden-1-one was dissolved in a mixed solvent of 150 ml of ethylacetate with 100 ml of acetic acid, this solution was let subjected to catalytic reduction at room temperature under 3 atmospheric hydrogen gas pressure in the presence of 1.5 g of palladium black as the hydrogenation catalyst. After the catalytic reduction, the catalyst was removed by filtration, and the filtrate was concentrated by removing the solvent under reduced pressure. The residue thus obtained was purified by a silica gel column chromatography (eluent: n-hexane: ethyl acetate=9:1) to obtain 8.5 g of 2,3-dihydro-4, 6-dimethyl-7-hydroxy-2-(4-methoxybenzyl)-1H-inden-1-one as in the form of colorless oily substance. |
Here is a chemical reaction formula: Reactants are:m2:[H-].[Na+];m4:[H-].[Na+];m6:[H-].[Na+];m3:CI;m7:CI;m5:CI;m1_m8:CC1=C2CC(C(C2=C(C(=C1)C)O)=O)CC1=CC=CC=C1;m1_m8:CN(C=O)C, Reagents are:, and Products are 0:CC1(C(C2=C(C(=CC(=C2C1)C)C)OC)=O)CC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 28.3 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-benzyl-1H-inden-1-one was dissolved in 350 ml of dimethylformamide, then 5.2 g of 60%-sodium hydride was added thereto at 55°-60° C. and the mixture was stirred for 40 minutes. Next 8 ml of methyl iodide was added thereto, and the whole mixture was heated to the same temperature for 1 hour. Followed by 5.2 g of 60%-sodium hydride was added and stirred for 40 minutes at the same temperature. Next, 8 ml of methyl iodide was further added and heated for 10 minutes at the same temperature. Furthermore, 5.2 g of 60%-sodium hydride was added to the reaction mixture and stirred for 55 minutes at the same temperature, and 8 ml of methyl iodide was added to the reaction mixture and heated to the same temperature for 3 hours and 20 minutes. After the reaction was completed, dimethylformamide was removed under a reduced pressure and the residue obtained was extracted with ethyl acetate. The extract was washed with water and with an aqueous solution saturated with sodium chloride in this order, then the solvent was removed under a reduced pressure to obtain the residue. The residue was purified by means of a silica gel column chromatography (eluent: n-hexane; ethyl acetate) to obtain 23.0 g of 2,3-dihydro-2,4,6-trimethyl-7 -methoxy-2-benzyl-1H-inden-1-one. |
Here is a chemical reaction formula: Reactants are:m6_m1_m2_m3_m4:OC=1C(=CC(=C2CCC(C12)=O)C)C(C=C)C1=CC=CC=C1;m6_m1_m2_m3_m4:Cl.NO;m6_m1_m2_m3_m4:N1=CC=CC=C1, Reagents are:m6_m1_m2_m3_m4:C(C)O;m6_m1_m2_m3_m4:C(C)O;m5:C(C)(=O)OCC, and Products are 0:OC=1C(=CC(=C2CCC(C12)=NO)C)C(C=C)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: An ethanol solution containing 120 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one, 45 of hydroxylamine hydrochloride and 200 ml of pyridine in 1,200 ml of ethanol was refluxed for 4 hours. After the reaction was completed, the reaction mixture was concentrated to dryness under a reduced pressure, then the residue thus obtained was dissolved in 2 liters of ethyl acetate and washed three times with 1 liter of water each time, and the residue was dried again under a reduced pressure. Recrystallized from ethyl acetate/n-hexane mixture to obtain 90 g of 2,3-dihydro-7-hydroxy-4-methyl-6-(1-phenyl-2-propenyl)-1H-inden-1-one oxime. Light yellow flake-like crystals. Melting point: 146° C. (Decomposed). |
Here is a chemical reaction formula: Reactants are:m3:C([O-])(O)=O.[Na+];m6_m2:[H][H];m1_m4:CC1=C2CC(C(C2=C(C(=C1)C)O)=NO)C1=CC=CC=C1, Reagents are:m6_m2:[Pt]=O;m1_m4:C(C)(=O)O;m5:O, and Products are 0:NC1C(CC2=C(C=C(C(=C12)O)C)C)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.00 Grams of 2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-inden-1-one oxime was dissolved in 55 ml of glacial acetic acid, and this solution was subjected to catalytic hydrogenation in the presence of 0.3 g of platinum oxide at room temperature under 4 atmospheric hydrogen gas pressure. The hydrogenation was terminated at the point when the stoichiometric amount of hydrogen was absorbed. The catalyst was removed by filtration and the filtrate thus obtained was concentrated. The residue thus obtained was dissolved in water and the pH of this solution was adjusted to about pH 8 by adding an aqueous solution of sodium bicarbonate, then extracted with 200 ml of chloroform. The chloroform extract was washed with water, dried with anhydrous magnesium sulfate, then concentrated under a reduced pressure. Recrystallized from ethanol to obtain 0.24 g of 1-amino-2,3-dihydro-4,6-dimethyl-7-hydroxy-2-phenyl-1H-indene Colorless needlelike crystals. Melting point: 135°-136° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClCC(=O)NCC1=CC(=C2CCC(C2=C1O)=O)C;m1_m2_m3_m4:Cl.NO;m1_m2_m3_m4:N1=CC=CC=C1;m1_m2_m3_m4:C(C)O;m5:O, Reagents are:, and Products are 0:[Cl-].OC=1C(=CC(=C2CCC(C12)=NO)C)C1=[N+](C=CC=C1)CC(=O)NC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 200 Grams of 6-chloroacetylaminomethyl-2,3-dihydro-7-hydroxy-4-methyl-1H-indene-1-one, 77.9 g of hydroxylamine hydrochloride, 300 ml of pyridine and 1,800 ml of ethanol were refluxed for 3 hours. After the reaction was completed, the solvent was removed by evaporation under a reduced pressure, then to the residue thus obtained was added 2 liters of water and the mixture was stirred vigorously, cooled and crystallized. The crystals were collected by filtration, washed with water, and recrystallized from water to obtain 167 g of (2,3-dihydro-7-hydroxy-1-hydroxyimino-4-methyl-1H-indene-6yl)-methylaminocarbonylmethylpyridinium chloride. Colorless flake-like crystals. Melting point: 279° C. (Decomposed). |
Here is a chemical reaction formula: Reactants are:m3:C([O-])(O)=O.[Na+];m2_m4:Cl.NC1C(CC2=C(C=C(C(=C12)O)C)C)(C)C;m1:ClC=1C=C(C=CC1)N1CCN(CC1)CC1CO1, Reagents are:m2_m4:C(C)O, and Products are 0:ClC=1C=C(C=CC1)N1CCN(CC1)CC(CNC1C(CC2=C(C=C(C(=C12)O)C)C)(C)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.21 Gram of 4-(3-chlorophenyl)-1-(2,3-epoxypropyl)piperazine was added to a solution containing 0.21 g of 1-amino-2,3-dihydro-7-hyroxy-2,2,4,6-tetramethyl-1H-indene hydrochloride in 10 ml of ethanol solution, and the mixture was refluxed for 5 hours. After the reaction was completed, the reaction mixture was concentrated by removing the solvent under a reduced pressure, the residue thus obtained was alkalified with 10%-sodium bicarbonate aqueous solution, then extracted with 100 ml of methylene chloride. The extract was washed there times with 100 ml of water each time, then dried with anhydrous magnesium sulfate. The methylene chloride extract was concentrated by removing the solvent under a reduced pressure, and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate: n-hexane=1:1) to obtain 0.21 g of 1-{3-[4-(3-chlorophenyl)-1-piperazinyl]-2-hydroxypropylamino}-2,3-dihydro-7-hydroxy-2,2,4,6-tetramethyl-1H-indene. |
Here is a chemical reaction formula: Reactants are:m1_m6:C(C)(C)(C)C1=CC=C(C=C1)O;m4:ClCC(=O)O;m2:[H-].[Na+];m3:[O-]C1=CC=CC=C1;m5:Cl, Reagents are:m1_m6:CN(C=O)C;m7:CN(C=O)C;m8:CN(C=O)C;m9:C(C)OCC, and Products are 0:C(C)(C)(C)C1=CC=C(OCC(=O)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 10.0 g (66.7 mmoles) p-tertbutylphenol in 50 ml dry dimethyl formamide was added, dropwise, to a mechanically stirred slurry of 8.4 g sodium hydride (as 50% oil dispersion) in 500 ml dry dimethyl formamide. To the phenoxide solution was added, dropwise, a solution of 6.3 g (66.3 mmoles) chloroacetic acid in 50 ml dry dimethyl formamide. The reaction mixture was stirred at room temperature for two hours. The reaction mixture was diluted with 200 ml diethyl ether and acidified with 3N hydrochloric acid. The aqueous layer was removed and washed with 200 ml diethyl ether. The organic layers were combined, dried (MgSO4) and evaporated to a white gummy residue which was dried in vacuo yielding p-t-butylphenoxyacetic acid, 9.0 g (65%). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)(C)(C)C1=CC=C(C=C1)O;m1_m2_m4_m3:[H-].[Na+];m1_m2_m4_m3:C(C=C)(=O)OCCCC, Reagents are:m1_m2_m4_m3:C1(=CC=CC=C1)NC1=CC2=CC=CC=C2C=C1, and Products are 0:C(C)(C)(C)C1=CC=C(OCCC(=O)OCCCC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 25 g (0.167 mole) p-tert-butylphenol, 0.2 g sodium hydride (as 50% dispersion in oil), 0.2 g N-phenyl-2-naphthylamine (as basic polymerization inhibitor) in 75.0 g (0.586 mole) butyl acrylate was heated at 125° C. for four hours. The temperature was then reduced to 100° C. and the excess acrylate distilled under gentle vacuum. The resulting oil was filtered through 900 g silica gel (90 to 200 mesh) using chloroform as eluant to yield 21.0 g pure butyl 3-(p-tert-butylphenoxy)-propionate (45%). |
Here is a chemical reaction formula: Reactants are:m4_m5_m8:[O-]C1=CC=CC=C1;m4_m5_m8:C(C)(=O)OCCCCCl;m1_m6:[H-].[Na+];m2_m7_m3:C(C)(C)(C)C1=CC=C(C=C1)O;m2_m7_m3:[O-]C1=CC=CC=C1, Reagents are:m4_m5_m8:CN(C=O)C;m1_m6:CN(C=O)C;m2_m7_m3:CN(C=O)C, and Products are 0:C(C)(=O)OCCCCOC1=CC=C(C=C1)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred slurry of 1.6 g sodium hydride (as 50% dispersion in oil) in 50 ml dry dimethyl formamide was added, drop-wise, a solution of 5.0 g p-tert-butylphenol (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution stirred under nitrogen until the phenoxide had totally formed. To the phenoxide was added a solution of 5.0 g 4-chlorobutyl acetate (33.3 mmoles) in 50 ml dry dimethyl formamide and the solution was stirred for fourteen hours. The reaction mixture was partitioned between water/toluene. The organic layer was removed, washed with water, then 1N sodium bicarbonate. The organic layer was removed, dried and evaporated to an orange oil, 5.6 g. The oil was chromatographed on 500 g, 90 to 200 mesh silica gel (CH2Cl2 eluent) yielding pure 4-(p-tert-butylphenoxy)-butyl acetate. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC1=CC=C(C=C1)C(CC(CCCO)=O)=O;m1_m2_m3_m4:N(N)C=1SC2=C(N1)C=CC=C2, Reagents are:m1_m2_m3_m4:N1=CC=CC=C1;m1_m2_m3_m4:CO, and Products are 0:S1C(=NC2=C1C=CC=C2)N2N=C(CC2(O)C2=CC=C(C=C2)Cl)CCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 6-(4-Chlorophenyl)-4,6-diketohexanol (7.2 g, 30 mM) was treated with 2-hydrazinobenzothiazole (4.96 g, 30 mM) in pyridine (5 ml) and MeOH (150 ml) at reflux for 2 hr and then allowed to stand at RT for 48 hr. The solvents were removed in vacuo and the crude residue purified by flash chromatography on silica with Et2O:Et3N (2.5%) as eluent. The title compound (1) was obtained as a pale yellow solid, (3.15 g, mp=132°-134° C.) upon recrystallization from Et2O:hexane. NMR(CDCl3) δ 3.2 (2H, C4 -H); MS, m/e 387 (M+). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC1=CC=C(C=C1)C(CC(CCCO)=O)=O;m1_m2_m3_m4:N(N)C=1SC2=C(N1)C=CC(=C2)OC, Reagents are:m1_m2_m3_m4:N1=CC=CC=C1;m1_m2_m3_m4:CO, and Products are 0:ClC1=CC=C(C=C1)C1=CC(=NN1C=1SC2=C(N1)C=CC(=C2)OC)CCCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 6-(4-Chlorophenyl)-4,6-diketohexanol (14.43 g, 60 mM) was treated with 2-hydrazino-6-methoxybenzothiazole (11.72 g, 60 mM) in pyridine (10 ml) and MeOH (300 ml) at reflux for 72 hr. Work-up as described in Example 1 followed by recrystallization from MeOH afforded the title compound 6 as a white solid (19.4 g), mp=123°-125° C.; NMR(CDCl3) δ 6.3 (s, 1H, C4 -H); MS, m/e 399 (M+). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:O=C(CCC(=O)O)CC(C=1C=NC=CC1)=O;m1_m4_m2:CCN(CC)CC;m3:Cl.COC1=CC=C(C=C1)NN, Reagents are:m1_m4_m2:CO, and Products are 0:Cl.COC1=CC=C(C=C1)N1N=C(C=C1C=1C=NC=CC1)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound 29 (2.21 g, 10 mM) in methanol (150 ml) containing Et3N (2 ml) was treated with 4-methoxyphenylhydrazine hydrochloride (1.85 g, 10.6 mM) at RT for 4 hr. The solvent was removed in vacuo and the residue was partitioned between 5% NaOH and Et2O. The basic aqueous layer was separated and acidified with 10% HCl to pH 2. Saturated brine was added and the aqueous layer was exhaustively extracted with CH2Cl2. The combined CH2Cl2 layers were concentrated to give the title compound 31 as a tan crystalline solid (Recry. Acetone, 1.87 g, 52%) mp=226°-228° C., MS, m/e 323 (M+). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C=1(O)C(=CC(O)=CC1)C1=CC=CC=C1COCC1=CC=CC=C1C=1C(O)=CC=C(C1)O;m1_m2_m3:BrCCOCCC;m1_m2_m3:[OH-].[Na+], Reagents are:, and Products are 0:C(C1=CC=CC=C1)OC1=CC=C(C=C1)OCCOCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Hydroquinone monobenzyl ether is reacted with 2-bromoethyl-n-propyl ether in aqueous sodium hydroxide and then purified over silica gel with toluene as eluent. The middle fraction gives 1-benzyloxy-4-(2-propoxy-ethoxy)benzene (used without further purification). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)O)F;m1_m2_m3:C(Cl)C1CO1;m1_m2_m3:N1CCCCC1, Reagents are:, and Products are 0:C(C1=CC=CC=C1)OC1=CC(=C(C=C1)OCC1CO1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.0 g of 4-benzyloxy-2-fluorophenol is reacted with 10 g epichlorhydrin and 0.2 ml piperidine for 90 minutes at 100°. After removal of the volatile material, 40 ml tetrahydrofuran and 20 ml 2M NaOH is added. After 1 hour stirring the solvent is evaporated and the residue partitioned between methylenechloride and water. The organic phase is purified over silica gel with toluene giving 4-benzyloxy-1-(2,3-epoxypropoxy)-2-fluorobenzene (colourless oil). |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[Na+];m3_m6:[N+](=O)([O-])C1=CC=C(CBr)C=C1;m2_m5:C(CCC)C=1NC2=C(N1)C=CC=C2C, Reagents are:m1_m4:CN(C)C=O;m3_m6:CN(C)C=O;m2_m5:CN(C)C=O, and Products are 0:C(CCC)C1=NC2=C(N1CC1=CC=C(C=C1)[N+](=O)[O-])C=CC=C2C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a slurry of NaH (60%, 0.21 g. 5.3 mmol) in DMF was added with stirring a solution of 2-butyl-4-methyl-benzimidazole (1 g. 5.3 mmol) in DMF (20 mL under nitrogen atmosphere. After the gas evolution was complete, the reaction mixture was cooled in ice and a solution of 4-nitrobenzyl bromide (1.5 g, 5.3 mmol) in DMF (5 mL) was added with stirring. The reaction mixture was allowed to warm up slowly to room temperature and stirred for 16 hours. DMF was distilled under reduced pressure and the residue was taken up in EtOAc, and the solution was washed with water. It was dried over MgSO4 and evaporated to give a solid which was chromatographed (CH2Cl2 /EtOAc 4/1-EtOAc) to give 1.5 g of a solid, MP 115°-116° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:C(CC(=O)OCC)(=O)OCC;m3:CC=1C=C(CCl)C=CC1C;m2:[Na], Reagents are:m1_m4:C(C)O;m5:C(C)OCC, and Products are 0:CC=1C=C(C=CC1C)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 70.0 ml of diethyl malonate dissolved in 400 ml of dry ethanol was added 10.0 g of metalic sodium. The reaction mixture was stirred for 30 minutes and cooled to 0° C; and 66.5 g of 3,4-dimethylbenzyl chloride was added thereto. This reaction mixture was stirred for 1 hour at room temperature, heated at the boiling temperature for 4 hours and concentrated under reduced pressure to produce residues, which were dissolved in ethyl ether. This ethereal solution was washed with water. To the residues obtained after a further concentration of the organic phase were added 500 ml of water and 170 g of KOH; and this mixture was heated at the boiling temperature for 24 hours. This mixture was concentrated under reduced pressure until about a half of the amount remained, and 200 ml of sulfuric acid was then slowly added thereto. The resultant solution was heated at the boiling temperature for 24 hours, extracted twice with 300 ml of ethyl ether and evaporated under reduced pressure to obtain solids, which were recrystallized from boiling hexane to provide 42.1 g of 3-(3,4-dimethylphenyl)propanoic acid as a white solid (yield 55%), having the characteristics of: m.p. 82° C.; NMR(CDCl3, 300 MHz) δ2.22(s, 3H, CH3), 2.24(s, 3H, CH3), 2.66(t, J=8 Hz, 2H, ArCH2), 2.89(t, J=8 Hz, 2H, CH2CO), 6.93~7.70(m, 3H, ArH). |
Here is a chemical reaction formula: Reactants are:m2_m5:O;m3:[H][H];m1_m4:C1OC=2C=C(C=CC(=O)O)C=CC2O1, Reagents are:m2_m5:[Pd];m1_m4:[OH-].[Na+], and Products are 0:C1OC=2C=C(C=CC2O1)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10.0 g of 3,4-methylenedioxycinnamic acid dissolved in 130 ml of 10% NaOH and 80 ml of distilled water was added 1.0 g of 5% Pd-C. This mixture was reacted at 40 psi until the consumption of hydrogen gas was ceased and then filtered through a Celite layer. The filtrate was acidified with concentrated hydrochloric acid, allowed to be cooled and filtered to give solids. The obtained solids were washed twice with 100 ml of cold water and dried to provide 9.8 g(yield 97%) of 3-(3,4-methylenedioxyphenyl) propanoic acid, having the characteristics of: NMR(CDCl3, 200 MHz) δ2.62(t, J=7 Hz, 2H, CH2), 2.88(t, J=7 Hz, 2H, CH2N), 5.93(s, 2H, CH2O2), 6.63-6.76(s, 3H, ArH). |
Here is a chemical reaction formula: Reactants are:m2_m5:[H-].[H-].[H-].[H-].[Li+].[Al+3];m3:[OH-].[Na+];m1_m4:C1OC=2C=C(C=CC2O1)CCC(=O)N, Reagents are:m2_m5:O1CCCC1;m6:O;m1_m4:O1CCCC1, and Products are 0:C1OC=2C=C(C=CC2O1)CCCN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 6.0 g of the above amide was dissolved in 100 ml of dry tetrahydrofuran, which was added dropwise to a suspension of 2.4 g of LiAlH4 in 150 ml of dry tetrahydrofuran. The reaction mixture was refluxed for 2 hours and 10 ml of 1N NaOH was added thereto. The mixture was filtered through a Celite layer to give solids, which were dissolved in 200 ml of distilled water. This solution was extracted twice with 200 ml of ethyl ether. The combined organic phase was dried over magnesium sulfate, concentrated and distilled under reduced pressure to provide 4.71 g(yield 85%) of 3-(3,4-methylenedioxyphenyl) propylamine, having the characteristics of: NMR(CDCl3, 200 MHz) δ1.34 (br s, 2H, NH2), 1.72(m, J=7 Hz, 2H, CH2), 2.57(t, J=7 Hz, 2H, CH2), 2.71(t, J=7 Hz, 2H, CH2N), 5.91(s, 2H, CH2O2), 6.59-6.74(s, 3H, ArH). |
Here is a chemical reaction formula: Reactants are:m4:Cl;m2_m3:C([O-])([O-])=O.[K+].[K+];m2_m3:C(C1=CC=CC=C1)Br;m1_m5:C(C)OC(CC1=CC(=C(C=C1)O)O)=O, Reagents are:m6:O;m1_m5:CC(=O)C, and Products are 0:C(C)OC(CC1=CC(=C(C=C1)O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5.79 g of 3,4-dihydroxylphenyl acetic acid ethyl ester dissolved in dry acetone were added 4.48 g of potassium carbonate and 4.15 ml of benzyl bromide. The mixture was heated to reflux until the starting materials were exhausted; and then the solvent was distilled off under reduced pressure. To the residues thus obtained was added 50 ml of water; and the mixture was acidified with concentrated hydrochloric acid and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure to obtain residues, which were purified by chromatography to provide 3.80 g (yield 45%) of 3-benzyloxy-4-hydroxyphenylacetic acid ethyl ester, having the characteristics of: NMR(CDCl3, 200 MHz) δ1.24(t, J=7 Hz, 3H, CH3), 3.45(s, 2H, CH2CO), 4.12(q, J=7 Hz, 2H, OCH2), 5.05(s, 2H, CH2Ph), 6.77-7.35(m, 6H, ArH). |