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Here is a chemical reaction formula: Reactants are:m4:C1CCCCC1.CCOC(=O)C;m1_m2_m5:NC(=N)N.Cl;m1_m2_m5:C[O-].[Na+];m3:NC1=NC=C(C=C1C#N)C#N, Reagents are:m1_m2_m5:CCO, and Products are 0:NC=1N=C(C2=C(N1)N=CC(=C2)C#N)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Guanidine·HCl (2.66 g, 27.8 mmol) was added to a solution of NaOMe (sodium methoxide) (1.50 g, 27.8 mmol) in absolute EtOH (180 mL). The mixture was stirred at 20°-23° C. for 15 minutes before 5 (2.00 g, 13.9 mmol) was added. After a 24-hour reflux period with rapid stirring, TLC (cyclohexane-EtOAc, 1:1) showed absence of 5. The solid filtered from the cooled mixture was washed on the funnel with H2O and EtOH; yield 95% (2.45 g). A sample of this material (1.0 g) was stirred with near-boiling Me2SO (dimethyl sulfoxide) (250 mL), and the slightly cloudy solution was filtered (Celite) to give a clear, pale-yellow filtrate which was then concentrated by evaporation in vacuo (to about 60 mL). Addition of EtOH (200 mL) gave 7 as a light yellow solid (880 mg); 1H NMR (Me2SO-d6) δ6.97 (2, NH2), 7.84 (s, NH2), 8.87 and 8.91 (two d, 5-H and 7-H, J=2 Hz). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3_m5:C(CCCCCCC)C=1C(=NC(=NC1Cl)C1=CC=C(C=C1)OCCCCC[C@H](CC)C)Cl;m1_m4_m2_m3_m5:[O-2].[Mg+2];m1_m4_m2_m3_m5:C(C)O, Reagents are:m1_m4_m2_m3_m5:[C].[Pd];m1_m4_m2_m3_m5:O, and Products are 0:C(CCCCCCC)C=1C=NC(=NC1)C1=CC=C(C=C1)OCCCCC[C@H](CC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Pour 1.88 g of optically active (s)-5-n-octyl-2-[4-(6-methyloctyloxy)phenyl]-4,6-dichloro-pyrimidine, 0.4 g of 10% palladium-carbon, 0.55 g of magnesium oxide, 60 ml of ethanol, and 45 ml of water, into a 200 ml flask, then add hydrogen under oil bath conditions at 50° C., until the logical amount of hydrogen has been absorbed. The catalyst is filtered and separated, then ether is extracted. After the ether layer is washed with water and with saturated salt water, and dried, the ether is evaporated. The resultant impure product is repeatedly refined, and 0.9 g of optically active (s)-5-n-octyl-2-[4-(6-methyloctyloxy)phenyl]-pyrimidine is obtained. |
Here is a chemical reaction formula: Reactants are:m2_m3:ClC1=CC(=C(C=C1)O)F;m2_m3:ClC1=C(C(=CC=C1)F)O;m7:ClC1=CC(=C(C=C1)O)F;m8:[OH-].[Na+];m9:[Na+].[Cl-];m1_m10:C([O-])([O-])=O.[K+].[K+];m6:ClC1=C(C(=C(C=C1)O)F)Cl;m5:ClC1=C(C(=CC=C1)F)O;m4:FC1=CC=C(C=C1)[N+](=O)[O-], Reagents are:m1_m10:CS(=O)C, and Products are 0:COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Cl)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred mixture of potassium carbonate (25.04 g; 0.18 mol) in DMSO (200 ml) under argon atmosphere was added an 8:2 mixture (25 g; 0.171 mol) (from Step 2A) of 4-chloro-2-fluorophenol (~20 g; 0.136 mol) and 2-chloro-6-fluorophenol (~5 g; 0.034 mol). To this mixture was added 4-fluoronitrobenzene (18.05 g; 0.128 mol) and the resulting mixture stirred at 100° C. for 30 minutes. At the end of this time, g.c. showed that the mixture contained (peak areas) ~10% of 2-chloro-6-fluorophenol, ~3% of a dichlorofluorophenol, a trace of 4-chloro-2-fluorophenol, and a single product peak. This mixture was poured into aqueous base (~1% NaOH) and the resulting mixture extracted with ether (2×300 ml). The ether extracts were combined, washed with water (an emulsion formed which required a little saturated aqueous NaCl to break), dried (MgSO4) and the solvent removed to given an orange-red oil (34 g). 19F NMR (CDCl3) showed that essentially a single isomer to be present. The material was subjected to Kugelrohr distillation (oven temp.=135°-145°) to give the desired product as a light yellow oil (32 g): RI=1.6038 @ 25° C. Recrystallization from hexane (freezer) gave the product as a white solid: m.p.=55°-57° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m3_m5:BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F;m1_m2_m3_m5:BrC(C(=O)OC)C;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m5:CS(=O)C, and Products are 0:COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (5.66 g, 0.02 mol) from Step V, methyl 2-bromoproprionate (3.34 g, 0.02 mol) and potassium carbonate (3.06 g, 0.22 mol) in DMSO (30 ml) was stirred, under an atmosphere of nitrogen, at room temperature for 18 hours. The mixture was poured into water (300 ml), and the resulting mixture extracted with ether (2×100 ml). The ether extracts were combined, washed with water (100 ml), dried (MgSO4), and the solvent evaporated to give the desired 2-[4-(4-bromo-2-fluorophenoxy)phenoxy]propionic acid; methyl ester as a yellow oil (6.0 g, 81%); RI=1.5628; NMR (CDCl3) was consistent with the assigned structure. The carbon and hydrogen content was as follows: |
Here is a chemical reaction formula: Reactants are:m1:BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F;m2_m3_m4_m5:CS(=O)(=O)[O-];m2_m3_m4_m5:C(C(O)C)(=O)OC;m2_m3_m4_m5:C([O-])([O-])=O.[K+].[K+], Reagents are:m6:O;m2_m3_m4_m5:CS(=O)C, and Products are 0:COC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of the 4-(4-bromo-2-fluorophenoxy)phenol (2.83 g, 0.01 mol), the methanesulfonate of S methyl lactate (18.2 g, 0.01 mol), and potassium carbonate (1.67 g, 0.012 mol) in DMSO (70 ml) was stirred at room temperature for 40 hours, then poured into water (700 ml). The mixture was extracted with ether (2×200 ml). Pentane (100 ml) was added to the combined ether extracts and the resulting solution washed with water (300 ml). The organic phase was dried (MgSO4) and the solvent evaporated to give a light yellow oil (~7 g). This oil was purified via prep HPLC (8:2 hexane-acetone) with the first peak being collected. Removal of the solvent gave the desired product enriched in the "R" enantiomer; Optical rotation=+20.34°@25° C. RI=1.5614@25° C.; NMR (CDCl3) was identical with that obtained in Example 4. No attempt was made to determine the optical purity of this material. |
Here is a chemical reaction formula: Reactants are:m6:C1(=CC=CC=C1)O;m4_m5:[Br-];m4_m5:C([O-])([O-])=O;m1_m2_m3_m8:ClC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F;m1_m2_m3_m8:BrC(CCC(=O)OCC)C;m1_m2_m3_m8:C([O-])([O-])=O.[K+].[K+];m7:Cl, Reagents are:m1_m2_m3_m8:CN(C)C=O, and Products are 0:ClC1=CC(=C(OC2=CC=C(OC(CCC(=O)OCC)C)C=C2)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred mixture of 4-(4-chloro-2-fluorophenoxy)phenol (2.3 g, 0.0103 mol), ethyl 4-bromopentanoate (2.01 g, 0.0103 mol), and potassium carbonate (1.46 g, 0.105 mol) in DMF (20 ml) was heated in an oil bath at 130° C. for one hour. Additional bromide (0.5 g) and carbonate (0.5 g) were added each hour for the next four hours. At the end of this period, gas chromatography indicated that most of the starting phenol had reacted. After cooling, the reaction mixture was poured into 4N HCl solution (200 ml), and the product extracted into a 1:1 mixture of ether-pentane (2×150 ml). The organic extracts were combined, washed with 10% NaOH solution (200 ml), dried (MgSO4), then the solvent evaporated. The resulting orange oil was purified via preparative HPLC (9:1 hexane/ethyl acetate) with the second peak being collected. Removal of the solvent gave the desired ester as a light yellow oil: RI=1.5344 @ 25° C. Calc: C, 62.21; H, 5.50. Found: C, 62.38; H, 5.33. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC1=CC(=C(OC2=CC=C(C=C2)O)C=C1)F;m1_m2_m3_m4:BrC(C(=CC(=O)OC)OC)C;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4:C(C)#N, Reagents are:m5:O, and Products are 0:BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 12.0 g (42.4 mmol) 4-(4-bromo-2-fluorophenoxy)phenol, 9.5 g (42.4 mmol) methyl 4-bromo-3-methoxy-2-pentenoate, 6.45 g (46.6 mmol) potassium carbonate and 180 ml acetonitrile was heated at reflux for 16 hours. The mixture was poured into water and extracted with ether. The combined ether extracts were washed with dilute aqueous NaOH, washed with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC eluting with 95:5 hexane:acetone, to give 10.5 g (58 percent) of the product as a clear colorless oil. Calc: C, 53.66; H, 4.27. Found: C, 53.28, H, 4.40. Structure was established on the basis of IR and NMR analysis. |
Here is a chemical reaction formula: Reactants are:m3:CCOCC;m4:C(C)(=O)O;m2:CC(C)C[AlH]CC(C)C;m1_m5:BrC1=CC(=C(OC2=CC=C(OC(C(=CC(=O)OC)OC)C)C=C2)C=C1)F, Reagents are:m6:C1(=CC=CC=C1)C;m7:O;m1_m5:C1(=CC=CC=C1)C, and Products are 0:BrC1=CC(=C(OC2=CC=C(OC(C(=CCO)OC)C)C=C2)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4.5 g (10.6 mmol) 4-(4-(4-bromo-2-fluorophenoxy)phenoxy)-3-methoxy-2-pentenoic acid, methyl ester in 25 ml toluene at -78° C. was added dropwise over a period of 30 min, 16.5 ml of 1.5M DIBAL-H in toluene, keeping the temperature below -60° C. The mixture was stirred for 21/2 hours at -78° C. To the mixture was added 17 ml of a 75:25:6 ether:acetic acid:water mixture, keeping the temperature below -60° C. The mixture was then allowed to warm to room temperature and the solid material was filtered off. The filtrate was washed twice with saturated NaHCO3 and once with water, dried over MgSO4 and the solvent was removed by rotary evaporation. The residue was purified by HPLC, eluting with 80:20 hexane:acetone, to give 3.1 g (74%) of the product as a pale yellow oil which was used immediately in the next reaction. |
Here is a chemical reaction formula: Reactants are:m4:BrC1=CC(=C(OC2=CC=C(OC(C(=O)Cl)C)C=C2)C=C1)F;m1_m2_m3:CC(CC(C)=O)=O;m1_m2_m3:C1=CC=CC=C1;m1_m2_m3:[Na], Reagents are:m6_m5:CCOCC;m6_m5:O, and Products are 0:C(C)(=O)C(C(C)=O)C(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.7 g (17 mmol) of 2,4-pentanedione, 30 ml of benzene and 0.26 g (11.3 mmol) of sodium was warmed at reflux for 3 hours. The reaction mixture was cooled to room temperature and a solution of 10 mmol of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanoyl chloride was added dropwise. The resulting mixture was warmed at reflux for 2.5 hours, stirred at room temperature overnight and poured into water and ether. The organic layer was separated, dried over MgSO4 and evaporated to dryness. The residue was purified by prep LC, eluting with 4:1 hexane:acetone. The product was taken up in ether and extracted with two portions of 1% aqueous NaOH. The combined aqueous layers were made acidic with aqueous HCl and extracted with ether. The ether layer was evaporated to dryness and the residue again purified by prep LC, eluting with 85:15 hexane:acetone. This gave a yellow oil which was thoroughly dried to leave 0.70 g product. Calc for C20H18BrFO5 : C, 54.93, H, 4.15. Found: C, 54.13, H, 4.30. |
Here is a chemical reaction formula: Reactants are:m5:[NH4+].[Cl-];m1_m6:C(C)(C)NC(C)C;m3_m8:C(C)(=O)OCC;m4_m9:BrC1=CC(=C(OC2=CC=C(OC(C=O)C)C=C2)C=C1)F;m2_m7:C(CCC)[Li], Reagents are:m1_m6:CCOCC;m3_m8:CCOCC;m4_m9:CCOCC;m2_m7:CCCCCC, and Products are 0:C(C)OC(CC(C(C)OC1=CC=C(C=C1)OC1=C(C=C(C=C1)Br)F)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.54 ml (11 mmol) of diisopropylamine in 20 ml of ether was cooled under N2 to -78° C. and 6.9 ml (11 mmol) of 1.6M n-butyllithium in hexane was slowly added. After 15 min of -78° C. 0.97 g (11 mmol) of ethyl acetate in 3 ml of ether was added dropwise. The resulting mixture was stirred at -78° C. for 15 min when a solution of 3.39 g (10 mmol) of 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propanaldehyde in 5 ml of ether was slowly added. The mixture was allowed to warm to room temperature, poured into aqueous NH4Cl and the aqueous phase separated and extracted with ether. The combined organic layers were dried over MgSO4 and evaporated to dryness and the residue purified by prep LC, eluting with 85:15 hexane:acetone. The resulting colorless oil was thoroughly dried to leave 2.99 g of product. Structure was confirmed by IR and NMR analysis. Calc. for C17H20BrFO5 : C, 53.41, H, 4.72. Found: C, 53.10, H, 4.66. |
Here is a chemical reaction formula: Reactants are:m3:ClCC(=O)Cl;m2:N1=CC=CC=C1;m1:ClC=1C=C(N)C=CC1F, Reagents are:m4:C1(=CC=CC=C1)C, and Products are 0:ClCC(=O)NC1=CC(=C(C=C1)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 130 ml. of toluene was added, with stirring, 24.0 g. (0.165 mole) of 3-chloro-4-fluoroaniline and 13.5 ml. (0.166 mole) of pyridine. The resulting solution was cooled to ca 0° C. and 13.2 ml. (0.166 mole) of 2-chloroacetyl chloride was added. The reaction mixture was stirred at room temperature for 5 hours and then it was extracted twice with 100 ml. of 1N hydrochloric acid, followed by 100 ml. of saturated sodium chloride solution. The resulting toluene solution was dried using magnesium sulfate, and then it was concentrated in vacuo to give 32.6 g. (88% yield) of N-(2-chloroacetyl)-3-chloro-4-fluoroaniline. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(C)N=C=O;m1:N1C(CC2=CC=CC=C12)=O, Reagents are:m3:C1(=CC=CC=C1)C, and Products are 0:C(C)(C)NC(=O)N1C(CC2=CC=CC=C12)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred suspension of 5.0 g. (37.6 mmole) of 2-oxindole in 50 ml. of toluene was added 8.0 g. (94.0 mmole) of isopropyl isocyanate, and the mixture was heated under reflux for 6 hours. The reaction mixture was allowed to cool and then it was stirred at room temperature overnight. The solvent was removed by evaporation in vacuo, and the residue was dissolved in hot cyclohexane. The solution was allowed to cool and the solid was collected by filtration, giving 7.0 g. of the title compound, m.p. 84°-85.5° C., as pink crystals. |
Here is a chemical reaction formula: Reactants are:m2_m4:C(CC)C=1C=C2C(=NC1)C(N(C2=O)C(C(=O)N)(C)C(C)C)=O;m3:O;m1:[OH-].[Na+], Reagents are:m2_m4:C1(=CC=CC=C1)C, and Products are 0:C(C)(C)C1(C(N=C2N1C(C=1C2=NC=C(C1)CCC)=O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: With the simultaneous addition of 0.5 g of powdered sodium hydroxide, a solution of α-[3-n-propyl-6H-pyrrolo[3,4-b]pyridine-5,7-dione-6-yl]-α-isopropyl-α-methyl-acetamide (m.p.: 82° C.) in 100 ml of toluene is heated under reflux for 2 hours in a water separator. After the reaction solution has cooled, it is filtered through silica gel and the filtrate is washed with ethyl acetate and then concentrated by evaporation. The residue is recrystallised from ethyl acetate/petroleum ether, affording 13.1 g of the title compound which melts at 116° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(CCCCCCCCCCCCC(C)C)(=O)O;m1_m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:C(CCCCCCCCCCCCC(C)C)(=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Isohexadecanoic acid (20 g, 0.078 mol) and thionyl chloride (7.2 ml, 0.0984 mol) were refluxed together gently for 1 hour to produce isohexadecanoyl chloride and the reaction was monitored by infra-red spectroscopy. Excess thionyl chloride was distilled away under rotary pump vacuum at reflux temperature. The acyl chloride was dissolved in n-hexane (50 ml) and slowly added to a chilled stirred solution of n-propylamine (7.05 ml, 0.0858 mol, m 0.1 excess). The solution also contained triethylamine (12 ml, 0.0858 mol, 0.1 excess) in n-hexane (200 ml) to ensure base conditions. After the addition was completed the reaction mixture was stirred at room temperature for 3 hours until all the acyl chloride was consumed. This was detected by monitoring the shift in the carbonyl frequency by infra-red spectroscopy. A product mixture was produced which consisted of N-(n-propyl)-isohexadecamide. The produce mixture was washed with water (2×200 ml), 6M hydrochloric acid (4×100 ml), water (100 ml), saturated aqueous sodium bicarbonate (1×100 ml), saturated aqueous sodium chloride (1×100 ml) and dried over MgSO4 before being filtered and rotary evaporated to yield a yellow oil (22.4 g, 96.5%). Infra-red spectroscopy (liquid film) detected absorption peaks at 3280 cm-1 (broad, strong), 3080 cm-1 strong, 1630 cm-1 (strong) and 1540 cm-1 (strong). |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:OC1=C(C=CC=C1)S(=O)(=O)N;m1_m2_m4:C([O-])([O-])=O.[K+].[K+];m3:BrC(C(=O)OC)C, Reagents are:m1_m2_m4:C(C)#N, and Products are 0:COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 34.6 g of 2-hydroxybenzenesulfonamide and 55.3 g of potassium carbonate are added to 800 ml of acetonitrile. With efficient stirring, 33.4 g of methyl 2-bromopropionate are added dropwise over 10 minutes and the suspension is then heated for 5 hours to 45° C. After the reaction mixture has cooled, the precipitated salts are isolated and the filtrate is concentrated in vacuo. The residue is recrystallised from ethanol, affording 41.8 g of 2-(1-methoxycarbonylethoxy)- benzenesulfonamide with a melting point of 140°-142° C. |
Here is a chemical reaction formula: Reactants are:m4:C(=O)(Cl)Cl;m1_m2_m5_m6:COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N;m1_m2_m5_m6:C(CCC)N=C=O;m3:C(=O)(Cl)Cl, Reagents are:m1_m2_m5_m6:N1(NCCCCCC1)C1CCCCCCC1;m1_m2_m5_m6:C=1(C(=CC=CC1)C)C, and Products are 0:COC(=O)C(C)OC1=C(C=CC=C1)S(=O)(=O)N=C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 12.9 g of 2-(1-methoxycarbonylethoxy)-benzenesulfonamide, 4.9 g of n-butylisocyanate and 0.1 g of diazabicyclooctane and 130 ml of xylene is refluxed for 30 minutes. Then 10 g of phosgene are passed into the solution at the same temperature over 90 minutes. Excess phosgene is expelled with nitrogen and the solution is then cooled and concentrated in vacuo, affording 17.7 g of 2-(1-methoxycarbonylethoxy)benzenesulfonyl isocyanate in the form of a brownish oil which can be further used without purification. |
Here is a chemical reaction formula: Reactants are:m2:C(C=C)OC1=C(C=CC=C1)S(=O)(=O)N;m1_m3:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m3:C(Cl)Cl, and Products are 0:O1C(C1)COC1=C(C=CC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 15.3 g of 3-chloroperbenzoic acid in 270 ml of absolute methylene chloride are added 14.2 g of 2-allyloxyphenylsulfonamide over 2 minutes. The solution is then heated to reflux for 3 hours, cooled, and then washed three times with saturated sodium carbonate solution and once with water. The organic phase is dried and concentrated, affording 11.9 g of 2-oxiranylmethoxyphenylsulfonamide with a melting point of 132°-133° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C(C)=O)OC1=C(C=CC=C1)S(=O)(=O)N;m1_m2_m3_m4:C(CO)O;m1_m2_m3_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C;m1_m2_m3_m4:C1(=CC=CC=C1)C, Reagents are:m5:C(C)(=O)OCC, and Products are 0:CC1(OCCO1)COC1=C(C=CC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.58 g of 2-(2-propanon-1-yloxy)phenylsulfonamide, 2 ml of ethylene glycol, 0.02 g of p-toluenesulfonic acid and 30 ml of toluene is heated for 7 hours to reflux while simultaneously separating the water of reaction. The cooled solution is taken up in 80 ml of ethyl acetate and the organic phase is washed with saturated sodium bicarbonate solution and water, dried and concentrated, affording 5 g of 2-(2-methyl-1,3-dioxolan-2-yl-methoxy)phenylsulfonamide in the form of a yellow viscous oil which can be further used without purification. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(#N)C1=CC=C(C=O)C=C1;m1_m2_m4_m3:OCC(C(C)O)CCCCC;m1_m2_m4_m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m2_m4_m3:C1=CC=CC=C1, and Products are 0:C(#N)C1=CC=C(C=C1)C1OCC(C(O1)C)CCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 0.1 mol of p-cyanobenzaldehyde, 0.1 mol of 3-hydroxymethyl-2-octanol, 200 ml of benzene and 150 mg of p-toluenesulfonic acid is boiled under a water separator until the reaction is complete. Usual working-up gives 2-p-cyanophenyl-5-n-pentyl-4-methyl-1,3-dioxane. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:C(C1=CC=CC=C1)(=O)Cl;m1_m3_m2_m4:N#CN.[Na], Reagents are:m1_m3_m2_m4:C(C)OCC;m1_m3_m2_m4:CCOCC, and Products are 0:C(C1=CC=CC=C1)(=O)NC#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Benzoylcyanamide was prepared by the addition of benzoyl chloride (6.33 g, 0.045 mol) in 100 ml of diethyl ether to a suspension of monosodium cyanamide (5.76 g, 0.090 mol) in 100 ml of ether at 4° C. The reaction was stirred overnight at room temperature and the pale yellow solid which formed was collected and dissolved in water. On acidification of the solution to pH 1, a precipitate formed which was collected and recrystallized from ethyl acetate (EtOAc)/petroleum ether (30-60° C) to give 2 (5.89 g, 89.7% yield), mp 140°-142° C. [reported mp 139°-140° C⟧ Anal. Calcd for C8H6H2O: C, 65.75; H, 4.11; N, 19.18. Found: C, 65.79; H, 4.35; N, 19.04. |
Here is a chemical reaction formula: Reactants are:m2_m4:N#CN.[Na];m1_m3:C12(CC3CC(CC(C1)C3)C2)C(=O)Cl, Reagents are:m2_m4:C1CCOC1;m1_m3:C1CCOC1, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C(=O)NC#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1-Adamantanecarbonyl chloride (1.99 g, 0.010 mol) in 50 ml of THF was added drop-wise to a suspension of sodium cyanamide (1.92 g, 0.030 mol) in 100 ml of THF with stirring at ice bath temperature. The reaction was allowed to proceed at 25° C. for 15 hours. The reaction mixture was then extracted with ethyl acetate (100 ml). The separated aqueous portion (pH 10.5) was acidified to pH 1.5 with 10% HCl and extracted with ethyl acetate (3×60 ml). The ethyl acetate extract was dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated in vacuo to dryness. The resulting white solid residue was triturated in a minimal amount of distilled water, filtered, and air-dried to give 1.74 g (85.2% yield) of crude 4 as white solid. This was recrystallized from ethyl acetate and petroleum ether to give 0.55 g (crop 1) of white crystalline powder. The filtrate was concentrated when further crystallization occurred to give 0.49 g (crop 2) of additional product giving a total yield of 50.9%, mp 168°-170° C. TLC: Rf =0.58 in EtOAc/petroleum ether/AcOH (50:100:1), detected by UV quenching (weak) and reddish orange color with ferricyanide spray reagent; IR (Nujol, cm-1), 3210 (NH), 2230 (C≡N), 1710 (C=O); NMR (Silanor C, δ from TMS) 1.62-2.2 (m, aliphatic CH's). Anal. Calcd for C12H16N2O: C, 70.56; H, 7.90; N, 13.71. Found: C, 70.59; H, 8.04; N, 13.66. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CC=CC=C1)(=O)Cl;m1_m2:[OH-].[Na+];m3_m4:N[C@@H](CC(C)C)C(=O)O, Reagents are:m3_m4:O, and Products are 0:C(C1=CC=CC=C1)(=O)N[C@@H](CC(C)C)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Benzoyl chloride (4.22 g, 0.030 mol) and 10% NaOH (12 ml, 0.030 mol) were added separately with vigorous stirring to a solution of L-leucine (3.94 g, 0.030 mol) in 150 ml of distilled water at ice bath temperature. The reaction was allowed to proceed at this temperature until the reaction mixture became clear (30 minutes); it was then extracted with ethyl acetate (2×100 ml). The aqueous layer was separated, acidified to pH 2 with 10% HCl, and extracted with ethyl acetate (3×50 ml). The ethyl acetate extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated in vacuo to yield quantitative amount of N-benzoyl-L-leucine as a semi-solid which was used directly for the following step. |
Here is a chemical reaction formula: Reactants are:m2_m3:[Cl-].[Mg+2].[Cl-];m2_m3:C(C)C(CO)CCCC;m1:C(C)O.[Cl-].[Mg+2].[Cl-], Reagents are:m4:C(C)O, and Products are 0:[Cl-].[Mg+2].[Cl-].C(C)C(CO)CCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a sample (50 g, 0.134 mole) of magnesium chloride ethanol adduct prepared as in Example 2 and having an ethanol:magnesium chloride ratio of 6 was added 60 ml of 2-ethyl-1-hexanol. The solution was then distilled at 120° C. to remove ethanol and heptane. Decane (97.7 g) was added to the resulting viscous solution to obtain the magnesium chloride-2-ethylhexanol adduct as a clear, colorless solution. It had a molar ratio of 2-ethylhexanol:magnesium chloride of 2.9 and still contained approximately 1% ethanol. |
Here is a chemical reaction formula: Reactants are:m1_m4:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)O)\C)OC)C)=O;m2_m3:S(=O)(Cl)Cl;m2_m3:CN(C=O)C, Reagents are:m1_m4:ClCCl, and Products are 0:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)Cl)\C)OC)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid (mycophenolic acid) (32.0 g) was dissolved in dichloromethane (250 ml), followed by the addition of thionyl chloride (25.0 ml) and dimethylformamide (0.3 ml). The reaction mixture was stirred at room temperature for 3 hours, after which the volatile components were removed under vacuum to afford E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid chloride as an oil. |
Here is a chemical reaction formula: Reactants are:m3:O;m2:C12(CC3CC(CC(C1)C3)C2)C(=O)Cl;m1_m4:OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O, Reagents are:m1_m4:N1=CC=CC=C1, and Products are 0:C12(CC3CC(CC(C1)C3)C2)C(=O)OC2=C3C(OCC3=C(C(=C2C/C=C(/CCC(=O)OCCN2CCOCC2)\C)OC)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Morpholinoethyl E-6-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate (10.0 g) was dissolved in pyridine (50.0 ml) followed by the addition of 1-adamantanecarbonyl chloride (10.0 ml). The mixture was stirred at room temperature for 90 minutes, then poured into water and extracted with ethyl acetate. The organic solution was dried and evaporated to give morpholinoethyl E-6-[1,3-dihydro-4-(1-adamantoyloxy)-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl]-4-methyl-4-hexenoate. |
Here is a chemical reaction formula: Reactants are:m1_m4:C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)O)\C)OC)C)=O;m2_m3:C1(CCCCC1)N=C=NC1CCCCC1;m2_m3:OCCN1CCOCC1, Reagents are:m1_m4:C1CCOC1, and Products are 0:C(N)(=O)OC1=C2C(OCC2=C(C(=C1C/C=C(/CCC(=O)OCCN1CCOCC1)\C)OC)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 1.0 g of E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoic acid dissolved in 20 ml of dry THF is added 0.59 g of dicyclohexylcarbodiimide and 0.037 g of N-(2-hydroxyethyl)morpholine. The mixture is left at room temperature for 6 hours, then evaporated to dryness. The residue is chromatographed on silica gel, eluting with 50:1 dichloromethane:methanol, to give morpholinoethyl E-6-(1,3-dihydro-4-carbamoyloxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-4-methyl-4-hexenoate. |
Here is a chemical reaction formula: Reactants are:m3:B.C1CCOC1;m1:B.C1CCOC1;m2:CC1(CCCCC1)C(=O)O, Reagents are:m4:C1CCOC1, and Products are 0:CC(O)C1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A three liter, three necked round bottom flask was equipped with a thermometer, magnetic stirrer, argon inlet and outlet adapters and a one liter addition funnel containing 922 ml of 1.0 molar BH3.THF. 1-Methyl cyclohexanecarboxylic acid (119.2 g; 0.84 m) was added to the reaction vessel and dissolved in 100 ml of THF. The reaction mixture was cooled with an ice bath to 5° C. and the BH3.THF was added dropwise over 25 min maintaining the temperature between 5°-15° C. After the addition was complete, the ice bath was removed. After about five min, the reaction exothermed and foamed violently. A much slower addition rate and constant cooling should help to avoid this exotherm. The reaction was allowed to stir for two hr at RT under nitrogen, then 150 ml of methanol was added cautiously. When the foaming ceased, the reaction was concertrated in vacuo using low heat and the residue was treated with 100 ml of 5% acetic acid. After stirring for thirty min, the reaction was transferred to a one liter separatory funnel, diluted with water (slurry dissolved) and extracted three times with ether. The combined ether extracts were washed twice with saturated sodium bicarbonate, twice with brine, dried over anhydrous magnesium sulfate, filtered through celite and concentrated in vacuo (low heat) to give 79.09 g of a clear water-white oil. The oil was distilled on a Kugelrohr apparatus at 75°-130° C. (25 mm of Hg). Most distilled at 90° C. to give 72.11 g of 1-methyl-1-cyclohexylmethanol. |
Here is a chemical reaction formula: Reactants are:m3:Cl.ClCCCN;m1_m2_m4:N1=CC=CC=2CCCCC12;m1_m2_m4:[NH2-].[Na+], Reagents are:m1_m2_m4:N, and Products are 0:N1=CC=CC=2CCCC(C12)CCCN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5,6,7,8-Tetrahydroquinoline (20 g) was added quickly to sodamide (17.6 g) in liquid ammonia (250 ml) to give a dark red coloured solution. 3-Chloropropylamine hydrochloride (28.9 g) was added in portions over four hours when loss of colour was permanent after which the reaction was stirred for a further 2 hours and then quenched with ammonium chloride (20 g). The liquid ammonia was allowed to evaporate and the residues were partitioned between chloroform and water. The pH was lowered to 6 and the chloroform layer was discarded. The aqueous layer was basified (pH 12-14), and extracted with chloroform, the chloroform extracts were dried, combined, evaporated and the residue was vacuum distilled to give 3-(5,6,7,8-tetrahydroquinol-8-yl)propylamine (7.58 g), b.p. 92°-94° C. at 0.1 mm Hg. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N1=CC=CC=2CCCC(C12)CCCN;m1_m2_m3:[N+](=O)([O-])NC=1NC=C(C(N1)=O)CC=1C=NC(=CC1)C, Reagents are:m1_m2_m3:N1=CC=CC=C1, and Products are 0:N1=CC=CC=2CCCC(C12)CCCNC=1NC=C(C(N1)=O)CC=1C=NC(=CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3-(5,6,7,8-tetrahydroquinol-8-yl)-propylamine (0.75 g, 0.0038 mole) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4(1H)-pyrimidone (0.99 g, 0.0037 mole) in pyridine (1 ml) was refluxed for 8 hr and evaporated to dryness. The residue was chromatographed on silica in 10% MeOH/CHCl3 then dissolved in hot CHCl3, filtered, and the product precipitated with petroleum ether 40°-60° C. to give the title compound (0.38 g), m.p. 75°-80° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC=1C=NC(=NC1)Cl;m1_m2_m3_m4:NC1=CC(=C(C=C1)O)Cl;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4:CS(=O)C, Reagents are:m5:O, and Products are 0:BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into a flask, 7.00 g of 5-bromo-2-chloropyrimidine, 5.19 g of 4-amino-2-chlorophenol, 9.98 g of potassium carbonate and 70 ml of dimethylsulfoxide were introduced, and reacted in a nitrogen atmosphere at 120° C. for 1.5 hours under stirring. After the completion of the reaction, the product was poured into water, and extracted with ethyl acetate. The extract was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and then purified by silica gel column chromatography, whereby 6.80 g of oily 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline was obtained. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m5:BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl;m2_m6:[N+](=O)([O-])C1=C(C(=O)N=C=O)C=CC=C1;m4:CO, Reagents are:m1_m5:O1CCOCC1;m2_m6:O1CCOCC1, and Products are 0:[N+](=O)([O-])C1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=NC=C(C=N2)Br)Cl)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into a flask, a solution obtained by dissolving 6.80 g of the above 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 30 ml of dioxane, was introduced, and a solution obtained by dissolving 5.76 g of 2-nitrobenzoylisocyanate in 30 ml of dioxane, was dropwise added thereto, and then the mixture was reacted at room temperature for 9 hours. After the completion of the reaction, the product was poured into water, subjected to filtration and washed with hot water. The crystals thereby obtained were put into methanol, and stirred, and then subjected to filtration again, to obtain 9.42 g of the desired product having a melting point of from 234 to 236° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m6:[N+](=O)([O-])C1=C(C(=O)NC(=O)NC2=CC(=C(C=C2)OC2=NC=C(C=N2)Cl)Cl)C=CC=C1;m1_m2_m3_m4_m6:ClC1=NC=C(C=N1)Cl;m1_m2_m3_m4_m6:NC1=CC(=C(C=C1)O)Cl;m1_m2_m3_m4_m6:C([O-])([O-])=O.[K+].[K+], Reagents are:m5:O;m1_m2_m3_m4_m6:CS(=O)C, and Products are 0:ClC=1C=C(N)C=CC1OC1=NC=C(C=N1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-(2-nitrobenzoyl)-N'-[3-chloro-4-(5-chloro-2-pyrimidinyloxy)phenyl]urea (1) Into a flask, 1.50 g of 2,5-dichloropyrimidine, 1.45 g of 4-amino-2-chlorophenol, 2.76 g of potassium carbonate and 15 ml of dimethylsulfoxide, were introduced, and reacted in a nitrogen atmosphere at 100° C. for 1.5 hours under stirring. After the completion of the reaction, the product was poured into water, and extracted with diethyl ether. The extract was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate, and then the solvent was distilled off. The crude product thereby obtained was purified and isolated by silica gel column chromatography to obtain 2.20 g of 3-chloro-4-(5-chloro-2-pyrimidinyloxy)aniline having a melting point of from 95 to 96° C. |
Here is a chemical reaction formula: Reactants are:m2_m4:BrC=1C=NC(=NC1)OC1=C(C=C(N)C=C1)Cl;m1_m3:C(=O)(Cl)Cl, Reagents are:m5:C(C)(=O)OCC;m2_m4:C(C)(=O)OCC;m1_m3:C(C)(=O)OCC, and Products are 0:BrC=1C=NC(=NC1)OC1=C(C=C(C=C1)N=C=O)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into a flask, a solution of 0.02 mol of phosgene in 30 ml of ethyl acetate was introduced. To this solution, a solution of 3 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chloroaniline in 10 ml of ethyl acetate was dropwise added at room temperature. The mixture was reacted at room temperature for 3 hours under stirring and further under reflux for one hour. After completion of the reaction, ethyl acetate was distilled off under reduced pressure, and the residue was vacuum-dried to obtain 3.10 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate having a melting point of from 63 to 68° C. (2) Into a flask, 1.22 g of 4-(5-bromo-2-pyrimidinyloxy)-3-chlorophenylisocyanate obtained in the above step was introduced, and 20 ml of toluene was added thereto. Further, 0.62 g of 2-nitrobenzamide was added under stirring. The mixture was reacted under reflux for 4 hours. After completion of the reaction, 5 ml of methanol was added to the reaction product, and the mixture was cooled. The precipitated crystals were collected by filtration to obtain 0.79 g of the desired product. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m2:[OH-].[Na+];m1_m4_m5:N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)OC)C=CC1)C1=CC=CC=C1, Reagents are:m6:O;m1_m4_m5:O;m1_m4_m5:CO, and Products are 0:N1=CC(=CC=C1)C(=CCOC=1C=C(C(=O)O)C=CC1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methyl 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoate (If-56, 1.5 g, 4.35 mmoles) was dissolved in a mixture of water (3 ml) and methanol (10 ml). To the solution was added sodium hydroxide (700 mg, 17.5 mmoles). The mixture was stirred for 2 hours at 60° C., which was then left standing for cooling. To the reaction solution was added water, the pH of which was adjusted to 5 with 1N hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried and the solvent was evaporated off. The residue was subjected to silica-gel column chromatography using ethyl acetate as eluant to yield 3-[3-(3-pyridyl)-3-phenyl-2-propenyloxy]benzoic acid (Ie-46) (1.15 g, 80%). Hydrolysis analogous to the above afforded substituted vinyl carboxylic acid derivatives (Ie-45-Ie-51, Ie-53, Ie-54) shown in Table 4-1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1;m1_m2_m3:CCN(CC)CCN1C2=C3C(=C(C=C2)CO)SC4=C(C3=N1)C=CC(=C4)Cl, Reagents are:m1_m2_m3:Cl, and Products are 0:Cl.N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-4, 300 mg was dissolved in 2N HCl (5 ml). The solution was concentrated under reduced pressure. Recrystallization of the resulting crystals from ethanol-isopropyl ether gave (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid hydrochloride (Ii-75) (285 mg), m.p. 163°-165° C. Physicochemical properties including other data are shown in Table 6. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C1=CC=CC=C1;m1_m2_m3:C(O)([O-])=O.[Na+], Reagents are:m1_m2_m3:O, and Products are 0:N1=CC(=CC=C1)/C(=C/CCCCC(=O)[O-])/C1=CC=CC=C1.[Na+], please give me the reaction condition of this formula. | The condition of this chemical reaction is: (E)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-4) (500 mg) and sodium hydrogen carbonate (160 mg) were added to water (5 ml) to make a homogeneous solution. The solution was concentrated under reduced pressure. The concentrate was pulverized by the use of ethanol-isopropylether to obtain sodium (E)-7-(3-pyridyl)-7-phenyl-6-heptenoate (Ii-76, 300 mg). The physico-chemical properties and other data of the product are shown in Table 6. |
Here is a chemical reaction formula: Reactants are:m3:[Br-].C(=O)(O)CCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1;m1_m2:[H-].[Na+];m1_m2:CS(=O)C;m4_m5:C1OC=2C=C(C(=O)C=3C=NC=CC3)C=CC2O1, Reagents are:m6:O;m4_m5:O1CCCC1, and Products are 0:C1OC=2C=C(C=CC2O1)/C(=C/CCCCC(=O)O)/C=1C=NC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sodium hydride (1 g, 60% in oil) was added to dimethyl sulfoxide (25 ml) under nitrogen and the mixture was heated at 85° C. with stirring for an hour. The reaction mixture was cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (5.2 g, 11 mmoles) was added gradually. The mixture was stirred for 10 minutes and a solution of 3-(3,4-methylenedioxybenzoyl)pyridine (2.5 g, 0.11 mole) in tetrahydrofuran (10 ml) was added dropwise thereto. After completion of addition, the mixture was further stirred at room temperature for 30 minutes. After completion of the reaction, water (100 ml was added and the neutral substance was extracted twice with toluene (50 ml). The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as the eluent. The eluate was concentrated and the residue was crystallized from ethyl acetate-isopropyl ether to give (Z)-7-(3,4-methylenedioxyphenyl)-7-(3-pyridyl)-6-heptenoic acid (0.4 g, 24.6%). Mp 90°-91° C. |
Here is a chemical reaction formula: Reactants are:m3:[Br-].C(=O)(O)CCCCC[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1;m4_m5:C(C1=CN=CC=C1)(=O)C=1SC=CC1;m1_m2:[H-].[Na+];m1_m2:CS(=O)C, Reagents are:m4_m5:O1CCCC1;m6:O, and Products are 0:N1=CC(=CC=C1)/C(=C/CCCCC(=O)O)/C=1SC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sodium hydride (60% in oil, 10 g, 0.25 mole) was added to dimethyl sulfoxide (250 ml) under argon and the mixture was stirred at 85° C. for an hour. The mixture was then cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (52 g, 0.11 mole) was added gradually with the temperature being maintained at 40° C. The resulting mixture was stirred for 10 minutes, and a solution of 2-nicotinoylthiophene (20 g, 0.11 mole) in tetrahydrofuran (60 ml) was added dropwise. After the addition, the mixture was stirred at room temperature for 30 minutes, and water (300 ml) was added. The aqueous solution was extracted twice with toluene (300 ml) to remove the neutral substance. The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as eluant and the eluate was concentrated. The resulting oily product was dissolved in ethyl acetate and the solution was allowed to stand overnight to give (Z)-7-(3-pyridyl)-7-(2-thienyl)-6-heptenoic acid (9 g, 29%). Mp 93°-94° C. |
Here is a chemical reaction formula: Reactants are:m5_m2_m3:C([O-])([O-])=O.[K+].[K+];m5_m2_m3:ClCC(C)=O;m1:CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C;m4:ClCC(C)=O, Reagents are:m5_m2_m3:C(C)#N, and Products are 0:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 70 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one are refluxed for 30 hours, whilst stirring, in 400 ml of acetonitrile with 100 g of potassium carbonate and 32 ml of chloroacetone. After the addition of a further 3.2 ml of chloroacetone, the reaction mixture is heated for a further 15 to 20 hours. The still warm reaction mixture is filtered, the residue thoroughly washed with acetone and the combined filtrate is concentrated by evaporation. The crystalline residue is recrystallised from toluene and yields 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one having a melting point of 125°-126°. |
Here is a chemical reaction formula: Reactants are:m4:[H][H];m1_m2_m3_m5_m6:C(C1=CC=CC=C1)N;m1_m2_m3_m5_m6:S(O)(O)(=O)=O;m1_m2_m3_m5_m6:O=C(COC1=CC=C(C(C(=O)N)=C1)O)C, Reagents are:m1_m2_m3_m5_m6:CO;m1_m2_m3_m5_m6:[Pt], and Products are 0:C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 55 g of benzylamine and 1.25 g of concentrated sulphuric acid are added to a solution of 104.5 g of 5-(2-oxopropoxy)salicylamide in 100 ml of methanol and hydrogenated in the presence of 3.0 g of Pt/C-catalyst at room temperature and atmospheric pressure until 1 equivalent of hydrogen has been absorbed. The catalyst is filtered off, approximately 10 g of powdered calcium carbonate are stirred into the solution and the solution is filtered again and concentrated by evaporation. The oil remaining crystallises from isopropanol. Repeated recrystallisation from isopropanol yields 5-[2-(benzylamino)propoxy]salicylamide having a melting point of 102°-104°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:O1C(COC2=CC=C(C=C2)OCCOC)C1;m1_m2_m3:C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:C(N)(=O)C=1C=C(OCC(C)N(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 10.2 g of 1-(2,3-epoxypropoxy)-4-(2-methoxyethoxy)benzene and 11.0 g of 5-[2-(benzylamino)propoxy]salicylamide in 200 ml of isopropanol is refluxed for 24 hours. By concentration of the solution by evaporation, crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is obtained as an oil which is used in its crude state for debenzylation. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C;m1_m2_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m3:BrCCBr, Reagents are:, and Products are 0:BrCCOC=1C=CC2=C(C(NC(O2)(C)C)=O)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 48.2 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one, 70 g of potassium carbonate and 250 ml of 1,2-dibromoethane is refluxed for 4 hours whilst stirring. The semi-liquid reaction mixture is extracted 3 to 4 times whilst hot with 1 liter of methanol each time; the combined methanol extracts are concentrated by evaporation and the residue is recrystallised from methanol. 6-(2-Bromoethoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one having a melting point of 190°-195° is obtained. |
Here is a chemical reaction formula: Reactants are:m2:C(N)(=O)C=1C=C(C=CC1O)CCCN(CC(COC1=CC=C(C=C1)OCCOC)O)CC1=CC=CC=C1;m3:Cl, Reagents are:m4:CO, and Products are 0:C(N)(=O)C=1C=C(C=CC1O)CCCNCC(COC1=CC=C(C=C1)OCCOC)O;0:Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 16 g of crude 1-[N-[3-(3-carbamoyl-4-hydroxyphenyl)propyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is hydrogenated analogously to Example 1. The hydrogenating solution is neutralised with a solution of hydrochloric acid gas in methanol, concentrated by evaporation and crystallised from acetone. In this manner 1-[3-(3-carbamoyl-4-hydroxyphenyl)propylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is obtained as a hydrochloride having a melting point of 194°-200°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m6_m4:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C;m1_m2_m5_m3_m6_m4:C(C1=CC=CC=C1)N;m1_m2_m5_m3_m6_m4:S(O)(O)(=O)=O;m1_m2_m5_m3_m6_m4:[H][H], Reagents are:m1_m2_m5_m3_m6_m4:CO;m1_m2_m5_m3_m6_m4:[Pt];m0_m7:C(C)(C)O, and Products are 0:C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 49.8 g of 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one and 21.4 g of benzylamine in 700 ml of methanol is hydrogenated with the addition of 0.5 g of concentrated sulphuric acid and 3 g of Pt/C-catalyst (5%) until the equivalent amount of hydrogen has been asborbed. Working up analogously to Example (1d) yields 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one having a melting point of 127°-129° (from isopropanol). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)OC1=CC=C(C=C1)OCC1CO1;m1_m2_m3:C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)N(CC(COC2=CC=C(C=C2)OCC2=CC=CC=C2)O)CC2=CC=CC=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 15.4 g of benzyl [4-(2,3-epoxypropoxy)phenyl]ether and 17.0 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one in 100 ml of isopropanol is refluxed for 24 hours, filtered and concentrated by evaporation. Trituration of the residue with approximately 200 ml of ether results in crystallisation of 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-benzyloxyphenoxy)propan-2-ol having a melting point of 149°-160° (in which the enantiomer pair A is present in greater amount). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(C)N;m1_m2_m3:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)NCC(COC2=CC=C(C=C2)C(NC)=O)O)C, Reagents are:m1_m2_m3:CO, and Products are 0:C(N)(=O)C=1C=C(OCC(C)NCC(COC2=CC=C(C=C2)C(NC)=O)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 80 ml of isopropylamine are added to a solution of 18.0 g of crude 1-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol in 300 ml of methanol and the solution is refluxed for 1 hour. The reaction mixture is concentrated by evaporation and the oil remaining is crystallised from 80 ml of isopropanol. 1-[2-(3-Carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol having a melting point of 172°-175° (diastereoisomeric mixture) is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)NC(COC=1C=CC2=C(C(NC(O2)(C)C)=O)C1)C;m1_m2_m3:O1C(COC2=CC=C(C(=O)NC)C=C2)C1, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)N(CC(COC2=CC=C(C=C2)C(NC)=O)O)CC2=CC=CC=C2)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 13.6 g of 6-(2-benzylaminopropoxy)-2,3-dihydro-2,2-dimethyl-4H-1,3-benzoxazin-4-one and 10.4 g of 4-(2,3-epoxypropoxy)-N-methylbenzamide in 80 ml of isopropanol is refluxed for 30 hours. The residue remaining after the solvent has been evaporated off is divided between ether and 2N hydrochloric acid. The acidic, aqueous phase is separated off, and, whilst cooling with ice, rendered alkaline with approximately 10% aqueous ammonia solution and extracted with ethyl acetate. By separating off, drying (MgSO4) and concentrating the ethyl acetate extract by evaporation, the crude 1-[N-[2-(2,3-dihydro-2,2-dimethyl-4-oxo-4H-1,3-benzoxazin-6-yloxy)-1-methylethyl]benzylamino]-3-(4-methylcarbamoylphenoxy)propan-2-ol is obtained as an oil which may be used without further purification for catalytic debenzylation. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C=C)OC1=C(OCC(CN)O)C=CC=C1;m1_m2:O=C(COC1=CC=C(C(C(=O)N)=C1)O)C;m3:O;m4:O, Reagents are:m5_m6:C1(=CC=CC=C1)C;m5_m6:C(C)(=O)O, and Products are 0:C(C=C)OC1=C(OCC(CNC(COC2=CC(=C(C=C2)O)C(N)=O)C)O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 11.2 g of 1-(2-allyloxyphenoxy)-3-aminopropan-2-ol and 10.5 g of 5-(2-oxopropoxy)salicylamide is boiled using a water separator in 200 ml of toluene with the addition of a few drops of acetic acid. After the splitting off of water has ceased (after about 2-3 hours), the solution is concentrated by evaporation, the dark red residue is dissolved in 300 ml of ethanol and a total of 5.7 g of sodium borohydride is added in portions whilst stirring. The temperature increases during this operation to 36°. The reaction mixture is stirred for a further 2 hours at 20°-30°, and left to stand overnight. Whilst cooling with ice, it is then brought to pH 3-4 with approximately 6N hydrochloric acid, filtered and concentrated by evaporation. The residue is divided between 100 ml of water and 100 ml of ethyl acetate, the aqueous phase is separated off, rendered alkaline with concentrated ammonia and extracted with 200 ml of ethyl acetate. Working up of the organic phase yields crude oily 1-(2-allyloxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]propan-2-ol as an enantiomer mixture. By slow crystallisation from isopropanol the two pure enantiomer pairs having melting points of 123°-125° and 98°-102° respectively are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:BrCCOC1=CC=C(C(C(=O)N)=C1)O;m1_m2:C(C=C)OC1=C(OCC(CN)O)C=CC=C1, Reagents are:m0_m3:C(C)(C)O, and Products are 0:C(C=C)OC1=C(OCC(CNCCOC2=CC(=C(C=C2)O)C(N)=O)O)C=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6.5 g of 5-(2-bromoethoxy)salicylamide and 8.9 g of 1-(2-allyloxyphenoxy)-3-aminopropan-2-ol is melted in an oil bath at 100° and stirred for 1 hour using a magnetic stirrer. The working up is carried out analogously to Example 11 and yields 1-(2-allyloxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]propan-2-ol having a melting point of 147°-148° (from isopropanol). |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1(OC2=C(C(N1)=O)C=CC(=C2)O)C;m1_m2:BrCCBr, Reagents are:m0_m3:C(C)(C)O, and Products are 0:CC1(OC2=C(C(N1)=O)C=CC(=C2)OCCBr)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.2 g of 2,3-dihydro-2,2-dimethyl-7-hydroxy-4H-1,3-benzoxazin-4-one are reacted analogously to Example (3a) with 84 ml of 1,2-dibromoethane and yield 2,3-dihydro-2,2-dimethyl-7-(2-bromoethoxy)-4H-1,3-benzoxazin-4-one having a melting point of 156°-158° (from isopropanol). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OC1=C(C(=O)N)C(=CC=C1)O;m1_m2_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m3:BrCCBr, Reagents are:m4:C(C)#N, and Products are 0:BrCCOC=1C=CC=C(C1C(=O)N)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 23.0 g of 2,6-dihydroxybenzamide, 20.7 g of potassium carbonate and 28.2 g of 1,2-dibromoethane is refluxed, whilst stirring, for 2-3 hours in 300 ml of acetonitrile. The reaction mixture is filtered whilst still warm, the filtrate concentrated by evaporation and the residue recrystallised from a little methanol. 6-(2-Bromoethoxy)salicylamide having a melting point of 120°-121° is obtained. |
Here is a chemical reaction formula: Reactants are:m2:O1C(COC2=C(C#N)C=CC=C2)C1;m1_m3:NC(COC1=CC=C(C(C(=O)N)=C1)O)(C)C, Reagents are:m1_m3:O1CCOCC1, and Products are 0:C(N)(=O)C=1C=C(OCC(C)(C)NCC(COC2=C(C=CC=C2)C#N)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The solution of 2.24 g of 5-(2-amino-2-methylpropoxy)salicylamide in 30 ml of dioxan is refluxed for 7 hours after the addition of 2.3 g of 2-(2,3-epoxypropoxy)benzonitrile, and then concentrated by evaporation. The residue is divided between 10 ml of 2N hydrochloric acid and 100 ml of ethyl acetate. The acidic aqueous phase is rendered alkaline with concentrated ammonia solution, the base is extracted with ethyl acetate and the solvent is evaporated off, whereupon an oil is obtained from which, by crystallisation from isopropanol and recrystallisation from ethyl acetate, 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-1,1-dimethylethylamino]-3-(2-cyanophenoxy)propan-2-ol having a melting point of 125°-126° is obtained. |
Here is a chemical reaction formula: Reactants are:m1:CC(COC1=CC=C(C(C(=O)N)=C1)O)(C)[N+](=O)[O-], Reagents are:m2:CO, and Products are 0:NC(COC1=CC=C(C(C(=O)N)=C1)O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 11.5 g 5-(2-methyl-2-nitropropoxy)salicylamide are hydrogenated in 150 ml of methanol at 40°-50° and 80 bar over 5 g of Raney nickel until hydrogen absorption ceases. By filtration and concentration of the filtrate by evaporation, crude 5-(2-amino-2-methylpropoxy)salicylamide is obtained, which, after standing for a relatively long period, crystallises from isopropanol and melts at 115°-117°. |
Here is a chemical reaction formula: Reactants are:m3_m1:N;m2:C(N)(=O)C=1C=C(OCC(C)NCC(COC2=CC(=C(C=C2)C(=O)OC)O)O)C=CC1O, Reagents are:m3_m1:O1CCOCC1, and Products are 0:C(N)(=O)C1=C(C=C(OCC(CNC(COC2=CC(=C(C=C2)O)C(N)=O)C)O)C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 50 ml of dioxan and 500 ml of concentrated ammonia solution is added to 21.5 g of 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol. The reaction mixture is stirred for 1-2 hours, and as soon as it is homogeneous, left to stand for 3 days at 20°-30°. By concentration by evaporation, 20 g of crude, crystalline 1-(4-carbamoyl-3-hydroxyphenoxy)-3-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethylamino]propan-2-ol is obtained as a diastereoisomeric mixture having a melting point of 180°-190°. A hydrochloride is formed which melts at 238°-243° (from ethanol/methanol). |
Here is a chemical reaction formula: Reactants are:m1:COC(C=1C(O)=CC(=CC1)OCC1CO1)=O;m2:C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C, Reagents are:m3:C(C)(C)O, and Products are 0:C(N)(=O)C=1C=C(OCC(C)N(CC(COC2=CC(=C(C=C2)C(=O)OC)O)O)CC2=CC=CC=C2)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: After 40 hours' boiling and working up analogously to Example (4a), 22.4 g of 4-(2,3-epoxypropoxy)salicylic acid methyl ester and 30 g of 5-(2-benzylaminopropoxy)salicylamide in 200 ml of isopropanol yield crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)-1-methylethyl]benzylamino]-3-(3-hydroxy-4-methoxycarbonylphenoxy)propan-2-ol as a light-coloured foam which is further processed as a crude product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:COC(C1=C(C(=CC=C1)O)O)=O;m1_m2_m4_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m4_m3:C(C1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1, Reagents are:m1_m2_m4_m3:C(C)#N, and Products are 0:COC(C=1C(O)=C(C=CC1)OCCN(CC1=CC=CC=C1)CC1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2,3-dihydroxybenzoic acid methyl ester is reacted in the presence of potassium carbonate in acetonitrile with 1.1 equivalents of 1-dibenzylamino-2-chloroethane for 18 hours at 82°. The crude 3-(2-dibenzylaminoethoxy)salicyclic acid methyl ester obtained after working up is put to further use without further purification. |
Here is a chemical reaction formula: Reactants are:m1:O1C(COC2=CC=C(C=C2)OCCOC)C1;m2:C(C1=CC=CC=C1)NCCOC1=C(C(C(=O)N)=CC=C1)O, Reagents are:, and Products are 0:C(N)(=O)C=1C(=C(OCCN(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By reacting 2.5 g of 1-(2,3-epoxypropoxy)-4-(2-methoxyethoxy)benzene with 2.9 g of crude 3-(2-benzylaminoethoxy)salicylamide obtained according to Example (25c), analogously to Example (4a), 1-[N-[2-(3-carbamoyl-2-hydroxyphenoxy)ethyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol is obtained as an oil which is further processed in this state |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:CC1(OC2=C(C(N1)=O)C=C(C=C2)O)C;m1_m2_m4:C(C=C)Br;m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m4:C(C)#N, and Products are 0:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC=C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 9.65 g of 2,3-dihydro-2,2-dimethyl-6-hydroxy-4H-1,3-benzoxazin-4-one and 9.1 g of allyl bromide in 150 ml of acetonitrile is refluxed for 5 hours, whilst stirring, with the addition of 10.3 g of dry potassium carbonate. The reaction mixture is filtered whilst warm, the filtrate is concentrated by evaporation and the remaining crystals are suction-filtered after trituration with ether. The crude 2,3-dihydro-2,2-dimethyl-6-(1-propen-3-yloxy)-4H-1,3-benzoxazin-4-one obtained in this manner melts at 137°-138°. |
Here is a chemical reaction formula: Reactants are:m1:C(N)(=O)C=1C=C(OCCCCN(CC(COC2=CC=C(C=C2)OCCOC)O)CC2=CC=CC=C2)C=CC1O, Reagents are:m2:CO, and Products are 0:C(N)(=O)C=1C=C(OCCCCNCC(COC2=CC=C(C=C2)OCCOC)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 25 g of crude 1-[N-[4-(3-carbamoyl-4-hydroxyphenoxy)butyl]benzylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol in 250 ml of methanol is hydrogenated and worked up analogously to Example 4. The resulting crystalline crude product is recrystallised from isopropanol and yields 1-[4-(3-carbamoyl-4-hydroxyphenoxy)butylamino]-3-[4-(2-methoxyethoxy)phenoxy]propan-2-ol having a melting point of 122°-124°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:O1C(COC2=C(C#N)C=CC=C2)C1;m1_m2_m4:NCCCCC1=CC=C(C(C(=O)N)=C1)O;m3:O, Reagents are:m1_m2_m4:CS(=O)C, and Products are 0:C(N)(=O)C=1C=C(OCCCCNCC(COC2=C(C=CC=C2)C#N)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.3 g of 2-(2,3-epoxypropoxy)benzonitrile are added to a solution of 6.7 g of 5-(4-aminobutyl)salicylamide in 60 ml of dimethyl sulphoxide and the mixture is stirred for 1 hour in a bath at 90°. The reaction mixture is poured into 300 ml of water and extracted twice with 200 ml of ethyl acetate each time. Working up analogously to Example 23 yields crude 1-[4-(3-carbamoyl-4-hydroxyphenoxy)butylamino]-3-(2-cyanophenoxy)propan-2-ol as a viscous oil, the IR- and 1H-NMR-spectra of which are in concordance with the assumed structure and the Rf-value of which is 0,51 according to thin-layer chromatography on silicagel using a mixture of ethylacetate-ethanol-conc. ammonia 24:12:4 as the eluent. |
Here is a chemical reaction formula: Reactants are:m1:C(N)(=O)C1=C(C=C(OCC(C)N(CC(COC2=CC=C(C=C2)NS(=O)(=O)C)O)CC2=CC=CC=C2)C=C1)O, Reagents are:m3:[Pd];m2:CO, and Products are 0:C(N)(=O)C1=C(C=C(OCC(C)NCC(COC2=CC=C(C=C2)NS(=O)(=O)C)O)C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 20.0 g of crude 1-[N-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethyl]-benzylamino]-3-(4-methanesulfonylamino-phenoxy)-2-propanol in 250 ml of methanol is hydrogenated, after the addition of 2.5 g of Pd/C catalyst (5%), under normal conditions until debenzylation is completed (DC control), for which an addition of a further 1.0 g of catalyst is required. The catalyst is filtered off; the filtrate is concentrated by evaporation, and the oil remaining behind is dissolved in a small amount of hot isopropanol. On cooling is obtained crystalline 1-[2-(4-carbamoyl-3-hydroxy-phenoxy)-1-methyl-ethylamino]-3-(4-methanesulfonylamino-phenoxy)-2-propanol, m.p. 147°-150° (diastereoisomeric mixture). |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)CCOCC2CC2)O)CC2=CC=CC=C2)C=CC1O;m1_m3_m4_m2:[H][H], Reagents are:m1_m3_m4_m2:CO;m1_m3_m4_m2:[Pd], and Products are 0:C(N)(=O)C=1C=C(OCCNCC(COC2=CC=C(C=C2)CCOCC2CC2)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 30 g of crude 1-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol in 600 ml of methanol is hydrogenated, with the addition of 4 g of a Pd/C catalyst (5%), under normal conditions until 1 mol-equivalent of hydrogen has been absorbed. By the addition of dioxane and by heating, the product which has already crystallised out is taken into solution; the catalyst is filtered off and the filtrate is concentrated by evaporation. Recrystallisation from isopropanol and then from methanol yields pure 1-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethylamino]-3-[4-[2-(cyclopropylmethoxy)-ethyl]-phenoxy]-2-propanol, m.p. 149°-150°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1(OC2=C(C(N1)=O)C=C(C=C2)OCC(C)=O)C, Reagents are:m1_m2_m3:O1CCOCC1;m1_m2_m3:Cl, and Products are 0:O=C(COC1=CC=C(C(C(=O)N)=C1)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 74 g of the resulting 2,3-dihydro-2,2-dimethyl-6-(2-oxopropoxy)-4H-1,3-benzoxazin-4-one in a mixture of 150 ml of dioxane and 450 ml of 2N hydrochloric acid are heated for 45 minutes on a water bath. The solvent is evaporated off, and the crystalline residue is triturated with water and then filtered off with suction. Recrystallisation from isopropanol yields 5-(2-oxo-propoxy)-salicylamide, which has a melting point of 152°-154°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:C(C1=CC=CC=C1)N;m1_m2_m3_m5:S(O)(O)(=O)=O;m1_m2_m3_m5:O=C(COC1=CC=C(C(C(=O)N)=C1)O)C;m4:[H][H], Reagents are:m6:[Pt];m1_m2_m3_m5:CO, and Products are 0:C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 55 g of benzylamine and 1.25 g of conc. sulfuric acid are added to a solution of 104.5 g of 5-(2-oxo-propoxy)salicylamide in 1000 ml of methanol, and the mixture is hydrogenated, in the presence of 3.0 g of a Pt/C catalyst under normal conditions until 1 equivalent of hydrogen has been absorbed. The catalyst is filtered off, and the solution is then stirred up with about 10 g of pulverised calcium carbonate; the mixture is again filtered, and concentrated by evaporation. The oil remaining behind crystallises from isopropanol. Repeated recrystallisation from isopropanol yields 5-[2-(benzylamino)-propoxy]-salicylamide, m.p. 102°-104°. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(CC1)COCCC1=CC=C(C=C1)OCC1CO1;m1_m2_m3:C(C1=CC=CC=C1)NC(COC1=CC=C(C(C(=O)N)=C1)O)C, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)CCOCC2CC2)O)CC2=CC=CC=C2)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 14.3 g of 1-[2-(cyclopropyl-methoxy)ethyl]-4-(2,3-epoxypropoxy)-benzene (German Offenlegungsschrift No. 2,649,605) and 16.3 g of 5-[2-(benzylamino)propoxy]-salicylamide in 200 ml of isopropanol is refluxed for 18 hours. The reaction mixture is concentrated by evaporation to leave crude 1-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-ethyl]-benzylamino]-3-[4-[2-(cyclopropylmethoxy)ethyl]-phenoxy]-2-propanol in the form of brown oil, which can be further processed without additional purification. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:C(N)(=O)C=1C=C(OCCN(CC(COC2=CC=C(C=C2)OCCO)O)CC2=CC=CC=C2)C=CC1O;m1_m3_m4_m2:[H][H], Reagents are:m1_m3_m4_m2:CO;m1_m3_m4_m2:[Pd], and Products are 0:C(N)(=O)C=1C=C(OCCNCC(COC2=CC=C(C=C2)OCCO)O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 23 g of crude 1-[N-[2-(3-carbamoyl-4-hydroxyphenoxy)ethyl]-benzylamino]-3-[4-(2-hydroxyethoxy)phenoxy]-2-propanol in 500 ml of methanol is hydrogenated, under normal conditions, with the addition of 2 g of 5% palladium on carbon catalyst, until hydrogen absorption has ceased. The catalyst is then removed by filtration and the filtrate is concentrated by evaporation under reduced pressure. The crystalline residue is stirred in a mixture of 50 ml of methanol and ether. The crystals so obtained are isolated by filtration and dried in vacuo, affording 1-[2-(3-carbamoyl-4-hydroxyphenoxy)ethylamino]-3-[4-(2-hydroxyethoxy)phenoxy]-2-propanol with a melting point of 150°-151° C. Reaction with the equivalent amount of hydrogen chloride, as solution in methanol, affords the hydrochloride with a melting point of 205°-206° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OCCOC1=CC=C(C=C1)O;m1_m2_m3:C(Cl)C1CO1;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], Reagents are:, and Products are 0:O1C(COC2=CC=C(C=C2)OCCO)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: With stirring, 13 g of crude 4-(2-hydroxyethoxy)phenol, 35 m of epichlorohydrin and 23.5 g of potassium carbonate are heated for 11/2 hours to reflux temperature. The reaction mixture is filtered and the filtrate is concentrated by evaporation under reduced pressure. The residual oil gradually congeals to a crystalline solid, which is recrystallised from isopropanol, affording 1-(2,3-epoxypropoxy)-4-(2-hydroxyethoxy)benzene with a melting point of 65°-67° C. Working up of the mother liquor yields further crystalline product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)OCC)=O;m1_m2_m3_m5:C(C)O;m1_m2_m3_m5:[OH-].[Na+];m4:Cl, Reagents are:m1_m2_m3_m5:O, and Products are 0:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)C)C(=O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.2 g of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate, 10 ml of ethanol, 15 ml of 10% sodium hydroxide solution and 10 ml of water is heated under reflux for 2 hours. 30 ml of 8M hydrochloric acid are added, the mixture is left to cool and the product is filtered off, washed with water and recrystallized from acetic acid to give 0.75 g of a solid melting at 284°-285° C. |
Here is a chemical reaction formula: Reactants are:m3:C(CO)Br;m1_m2_m4:FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m4:CN(C=O)C, and Products are 0:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCO)C(=O)OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2 g (0.0076 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-caboxylate and 1.85 g (2×0.0076 mol) of potassium carbonate in 20 ml of dimethylformamide is heated for 30 minutes at 60° C. and left to cool, 3.35 g (4×0.0076 mol) of ethylene bromohydrin are added, the mixture is heated at 80°-90° C. for 10 hours, active carbon is added, the mixture is filtered hot, the filtrate is evaporated to dryness, water is added and the precipitate formed is filtered off and washed with water. It is recrystallized from dimethylformamide to give 1.2 g of a solid melting at 237°-239° C. |
Here is a chemical reaction formula: Reactants are:m2:P(=O)(Cl)(Cl)Cl;m1:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCO)C(=O)OCC)=O, Reagents are:m3:C(Cl)(Cl)Cl, and Products are 0:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCCl)C(=O)OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.5 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-(2-hydroxyethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate are suspended in 30 ml chloroform, 3 ml of Cl3PO are added, the mixture is kept at room temperature for 2 hours and evaporated to dryness, the residue is redissolved in chloroform, the resulting solution is washed with a sodium bicarbonate solution and then with water and evaporated, and the precipitate is recrystallized from dimethylformamide to give 3.3 g of a solid melting at 254°-256° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:FC=1C=C2C(=C(C=NC2=CC1N1C=CC=C1)C(=O)OCC)O;m1_m2_m3:C([O-])([O-])=O.[K+].[K+];m1_m2_m3:CCCBr, Reagents are:m4:O, and Products are 0:FC=1C=C2C(C(=CN(C2=CC1N1C=CC=C1)CCC)C(=O)OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3 g (0.01 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-4-hydroxyquinoline-3-carboxylate, 2.8 g (0.02 mol) of potassium carbonate and 6 g (0.04 mol) of n-propyl bromide is heated for 5 hours at 80°-90° C. and left to cool, water is added and the precipitate formed is filtered off, washed with water and recrystallized from ethanol to give 2.4 g of a solid melting at 128°-130° C. |
Here is a chemical reaction formula: Reactants are:m2:COC1(OCCC1)OC;m3:O;m1_m4:FC1=C(C(=O)O)C=C(C(=C1)N)F, Reagents are:m1_m4:C(C)(=O)O, and Products are 0:FC1=C(C(=O)O)C=C(C(=C1)N1C=CC=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5.2 grams (0.03 mol) of 2,5-difluoro-4-aminobenzoic acid, melting at 250°-3°, are dissolved in 60 ml of glacial acetic acid, and 4 grams (0.03 mol) of dimethoxytetrahydrofuran are added. The mixture is heated at the boil for 10 minutes, 20 ml of water are added and the resulting mixture is left to cool. The precipitate formed is filtered off and washed with water to give 5.3 grams of a solid melting at 196°-8° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(OCC)([O-])[O-];m1_m2_m4:FC1=C(C(=O)CC(=O)OCC)C=C(C(=C1)N1C=CC=C1)F;m3:C1(CC1)N, Reagents are:m1_m2_m4:C(C)(=O)OC(C)=O, and Products are 0:C1(CC1)NC=C(C(=O)OCC)C(C1=C(C=C(C(=C1)F)N1C=CC=C1)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1 g (0.0068 mol) of ethyl orthoformate is added to a solution of 1.1 g (0.00315 mol) of ethyl 2,5-difluoro-4-(pyrrol-1-yl)benzoylacetate in 3 ml of acetic anhydride and the mixture is refluxed for 3 hours. It is evaporated to dryness, the residue is dissolved in 10 ml of ethanol, 0.3 ml (0.0034 mol) of cyclopropylamine is added and the mixture is left at room temperature for 1 hour. It is evaporated to dryness and the oily residue is extracted with 3×30 ml of boiling hexane. The hexane fractions are concentrated to 20 ml and left for 12 hours at 5° C. to give 0.41 g of crystals melting at 90°-2° C. |
Here is a chemical reaction formula: Reactants are:m4_m1_m2:Br.NCCC1=CC(O)=C(O)C=C1;m4_m1_m2:C(C1=CN=CC=C1)(=O)O;m3:C1(CCCCC1)N=C=NC1CCCCC1, Reagents are:m4_m1_m2:N1=CC=CC=C1, and Products are 0:C(C1=CN=CC=C1)(=O)NCCC1=CC(O)=C(O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a pyridine solution containing 11.7 g (0.05 mol) dopamine hydrobromide and 6.15 g (0.05 mol) nicotinic acid at 0° C. were added 10.3 g (0.05 mol) dicyclohexylcarbodiimide (DCC). The reaction mixture was stirred at room temperature for 24 hours and the formed dicyclohexylurea was removed by filtration. The pyridine was removed in vacuo and the residue was crystallized from water at 0° C. The product was isolated by filtration and dried over phosphorous pentoxide. Recrystallization from isopropanol gave 9.0 g (0.035 mol), 70% N-nicotinoyldopamine, m.p. 159°-162° C.; aqueous solution of the compound gave a green color with Fe+3 and reduced AgNO3 ; ir (KBr) 3300, 2960, 1725, 1630, 1590, 1520, 1430, 1290, 1190, 1115, 720 and 710 cm-1 ; NMR (d6 -DMSO) δ 9.25-6.25 (m, 7H), 3.3 (m, 2H) and 2.65 (m, 2H) ppm. Anal. (C14H14N2O3) C, H, N. |
Here is a chemical reaction formula: Reactants are:m3:CI;m1_m4_m2:C(C1=CN=CC=C1)(=O)NCCC1=CC(O)=C(O)C=C1;m1_m4_m2:CI, Reagents are:m1_m4_m2:CO, and Products are 0:[I-].C[N+]1=CC(=CC=C1)C(NCCC1=CC(=C(C=C1)O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2 g (7.7 mmol) of nicotinoyldopamine in 40 ml of dry methanol were added 2.5 g (17.6 mmol) of methyl iodide. The reaction mixture was refluxed with stirring for 6 hours. Methyl iodide (1.5 g, 1.05 mmol) was added and refluxing was continued overnight. Methanol was removed and ethyl acetate was added, affording yellowish crystals of the desired product. Yield 2.4 g (77%), m.p. 173°-174° C. |
Here is a chemical reaction formula: Reactants are:m3:C(C)O;m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1;m1_m2:N\C(=C/C(=O)OC)\C, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)-ethyl 2-(3-nitrobenzilidene)acetylacetate and 4.19 g (0.04 moles) of methyl 3-aminocrotonate are heated for 4 hours under reflux in 40 ml of ethanol. The solution is cooled to 7° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in isopropanol--at 202°-204° C. The yield was 68% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1;m1_m2:N\C(=C/C(=O)OCCSC)\C;m3:C(C)O, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 6.37 g (0.04 moles) of 2-methylthioethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol during 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-methylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 76° C.-80° C. The yield is 80% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1;m1_m2:N\C(=C/C(=O)OCCSCC)\C;m3:C(C)O, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15 g (0.04 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 6.88 g (0.04 moles) of 2-ethylthioethyl 3-aminocrotonate were heated under reflux in 35 ml of ethanol for 8 hours. The solution was then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-ethylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as a yellow powder melting--after recrystallisation in ethanol--at 100°-104° C. The yield is 60% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m3:C(C)O;m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC2=CC=C(C=C2)NC(C)=O)C=CC1;m1_m2:N\C(=C/C(=O)OCCSC(C)C)\C, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCOC1=CC=C(C=C1)NC(C)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCCSC(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 12 g (0l03 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenylidene)acetylacetate and 5.92 g (0.03 moles) of 2-isopropylthioethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-isopropylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in aqueus ethanol--at 142°-144° C. The yield was 42% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCNC(C2=CN=CC=C2)=O)C=CC1;m1_m2:N\C(=C/C(=O)OC)\C;m3:C(C)O, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCNC(C1=CN=CC=C1)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 25 g (0.07 moles) of 2-(N-nicotinoylamino)ethyl 2-(3-nitrobenzylidene)acetylacetate and 7.51 g (0.07 moles) of methyl 3-aminocrotonate are heated uner reflux in 70 ml of ethanol for 45 minute. The solution is the cooled to room temperature to obtain 2-(N-nicotinoylamino)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 207°-209° C. The yield is 70% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m3:C(C)O;m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OC2CC(CC(C2)C)(C)C)C=CC1;m1_m2:N\C(=C/C(=O)OCC)\C, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OC1CC(CC(C1)C)(C)C)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 21.87 g (0.06 moles) of 3,3,5-trimethylcyclohexyl 2-(3-nitrobenzylidene)acetylacetate and 7.84 g (0.06 moles) of ethyl 3-aminocrotonate are heated under reflux in 60 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 3,3,5-trimethylcyclohexyl 2,6-dimethyl-5-ethoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in ethanol--at 125°-129° C. The yield is 37% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC(=O)CC(=O)OCCOC(C2=CC=C(C=C2)NC(C)=O)=O)C=CC1;m1_m2:N\C(=C/C(=O)OC)\C;m3:C(C)O, Reagents are:, and Products are 0:CC=1NC(=C(C(C1C(=O)OCCOC(C1=CC=C(C=C1)NC(C)=O)=O)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 20 g (0.05 moles) of 2-(4-acetylaminobenzoyloxy)ethyl 2-(3-nitrobenzylidene)acetylacetate and 5.23 g (0.05 moles) of methyl 3-aminocrotonate are heated under reflux in 45 ml of ethanol for 8 hours. The solution is then cooled to room temperature to obtain 2-(4-acetylaminobenzoyloxy)ethyl 2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as a yellow powder melting at 190°-193° C. The yield is 94% of the theoretical yield. |
Here is a chemical reaction formula: Reactants are:m4_m6:ClCC1=CC=CC2=CC=CC=C12;m1_m2_m3_m5:C(#N)CCC(C(=O)O)CC1=CC=CC2=CC=CC=C12;m1_m2_m3_m5:C(C)OC(C(C(=O)OCC)CCC#N)=O;m1_m2_m3_m5:[H-].[Na+], Reagents are:m4_m6:CN(C)C=O;m1_m2_m3_m5:CN(C)C=O, and Products are 0:C(C)OC(C(C(=O)OCC)(CC1=CC=CC2=CC=CC=C12)CCC#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Cyano-2(R,S)-α-naphthylmethylbutyric acid: 2.13 g of 2-cyanoethylmalonic acid diethyl ester are added to a suspension of 0.48 g of sodium hydride dispersion in 25 ml of DMF. The reaction mixture is stirred for 2 hours at 80° and then, at room temperature, 1.77 g of α-chloromethylnaphthalene in 5 ml of DMF are added. The mixture is further stirred for 16 hours at 50° and then concentrated by evaporation. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate and concentrated by evaporation, leaving 2-cyanoethyl-α-naphthylmethylmalonic acid diethyl ester. |
Here is a chemical reaction formula: Reactants are:m3_m4_m5:ClCC#N;m3_m4_m5:[H-].[Na+];m1_m2:C(#N)CC(C(=O)O)CC1=CC=CC2=CC=CC=C12;m1_m2:C(C)OC(C(C(=O)OCC)CC1=CC=CC2=CC=CC=C12)=O, Reagents are:m3_m4_m5:CN(C)C=O, and Products are 0:C(C)OC(C(C(=O)OCC)(CC1=CC=CC2=CC=CC=C12)CC#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2(R,S)-Cyanomethyl-3-α-naphthylpropionic acid: 3.0 g of α-naphthylmethylmalonic acid diethyl ester and, after 30 minutes, 0.6 ml of chloroacetonitrile are added to a stirred suspension of 0.44 g of sodium hydride dispersion in 50 ml of DMF. The reaction mixture is stirred for 1 hour at 50° and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate, washed with 0.1N hydrochloric acid and water, dried over sodium sulphate, concentrated by evaporation and purified by chromatography on silica gel with toluene, yielding cyanomethyl-(α-naphthylmethyl)-malonic acid diethyl ester. |
Here is a chemical reaction formula: Reactants are:m3_m4:C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O;m3_m4:C(C=C)#N;m1_m2:C(#N)CCC(C(=O)O)OC1=CC=CC2=CC=CC=C12;m1_m2:[OH-].[K+], Reagents are:m5:C(C)(=O)OCC, and Products are 0:C(C)OC(C(C(=O)OCC)(OC1=CC=CC2=CC=CC=C12)CCC#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Cyano-2(R,S)-α-naphthoxybutyric acid: 0.11 ml of a 50% aqueous KOH solution is added at 0°, while stirring, to a mixture of 5.0 g of α-naphthoxymalonic acid diethyl ester and 1.09 ml of acrylonitrile. The reaction mixture is stirred for 5 days at room temperature and then dissolved in ethyl acetate. The ethyl acetate solution is washed with 2N sodium bicarbonate solution, 2N hydrochloric acid and brine, dried over sodium sulphate and concentrated by evaporation, leaving (2-cyanoethyl)-α-naphthoxymalonic acid diethyl ester. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:C1(=CC=CC2=CC=CC=C12)O;m1_m4_m2_m5:[H-].[Na+];m3_m6:C(C)OC(C(C(=O)OCC)Br)=O, Reagents are:m1_m4_m2_m5:CN(C)C=O;m1_m4_m2_m5:CN(C)C=O;m3_m6:CN(C)C=O, and Products are 0:C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 25 g of 1-naphthol in 50 ml of DMF is slowly added dropwise to a solution of 7.6 g of sodium hydride dispersion in 300 ml of DMF. The suspension is stirred for 30 minutes and subsequently 41.5 g of bromomalonic acid diethyl ester in 50 ml of DMF are added dropwise. The reaction mixture is further stirred for 16 hours at room temperature and then concentrated by evaporation in a high vacuum. The residue is dissolved in ethyl acetate and washed with 2N sodium hydroxide solution, water and brine, dried over sodium sulphate and concentrated by evaporation. The residue is distilled at 145°-170°/2.6 Pa and yields α-naphthoxymalonic acid diethyl ester in the form of an orange-coloured oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m6:C(N)(=O)CCC(C(=O)O)OC1=CC=CC2=CC=CC=C12;m1_m2_m3_m4_m6:N12CCCCCC2=NCCC1;m1_m2_m3_m4_m6:C(C)OC(C(C(=O)OCC)OC1=CC=CC2=CC=CC=C12)=O;m1_m2_m3_m4_m6:C(C=C)(=O)N;m5:Cl, Reagents are:m1_m2_m3_m4_m6:C(C)#N;m7:O, and Products are 0:C(C)OC(C(C(=O)OCC)(OC1=CC=CC2=CC=CC=C12)CCC(N)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Carbamoyl-2(R,S)-α-naphthoxybutyric acid: 1.49 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene are added to a solution of 3 g of α-naphthoxymalonic acid diethyl ester (Example 36a) and 0.71 g of acrylamide in 5 ml of acetonitrile and the whole is stirred at room temperature for 24 hours. 25 ml of water are added to the reaction mixture, which is adjusted to pH 2 with 2N hydrochloric acid and extracted with ether. The ethereal phases are washed with water and brine, dried over sodium sulphate and concentrated by evaporation, leaving (2-carbamoylethyl)-α-naphthoxymalonic acid diethyl ester. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(C)OC(C)C;m1_m4_m2_m5:Cl;m1_m4_m2_m5:C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC, Reagents are:m1_m4_m2_m5:C(C)O;m1_m4_m2_m5:C(C)O, and Products are 0:Cl.C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.85 ml of a 6.4N hydrogen chloride solution in ethanol were added to a solution of 5.1 g of the product of Example 6 in 5.1 ml of ethanol and then isopropyl ether was added thereto. The mixture was filtered and the recovered product was empasted several times with isopropyl ether, filtered and was dried. The product was dissolved in 350 ml of tetrahydrofuran and the solution was filtered and concentrated to a volume of 75 ml. The mixture was cooled, iced and filtered and the recovered product was washed with tetrahydrofuran and dried to obtain 3.3 g of 3-ethyl-5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole hydrochloride melting towards 150° C. with decomposition. |
Here is a chemical reaction formula: Reactants are:m3:COC1=CC=C(C(=O)NNC(C)=O)C=C1;m1:NC1=CC=CC=C1;m2:[P], Reagents are:m4:ClC1=C(C=CC=C1)Cl, and Products are 0:COC1=CC=C(C=C1)C1=NN=C(N1C1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the procedure of Step B in Example 1, 26.3 ml of aniline, 150 ml of o-dichlorobenzene, 4.65 ml of phosphorus trichlorode and 10 g of N-(4-methoxybenzoyl)-N'-acetyl-hydrazine [prepared by process of J. Org., Vol. 19 (1954), p. 194-201] were reacted to obtain 7.1 g of 3-(4-methoxyphenyl)-4-phenyl-5-methyl -4H-1,2,4-triazole melting at 140°-141° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:COC1=CC=C(C(=S)NC2=CC=C(C=C2)[N+](=O)[O-])C=C1;m1_m3_m2:O.NN, Reagents are:m1_m3_m2:C(C)O, and Products are 0:COC1=CC=C(C=C1)C(NC1=CC=C(C=C1)[N+](=O)[O-])=NN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 10 g of 4-methoxy-4'-nitrothiobenzanilide [prepared by process of Ann. Chem., Vol. 716 (1968), p. 209-211], 100 ml of ethanol and 15 ml of hydrazine hydrate was heated to reflux and then was allowed to return to room temperature and was filtered. The product was washed with ethanol and dried at 80° C. under reduced pressure to obtain 7.9 g of 4-methoxy-N-(4-nitrophenyl)-benzene-carbohydrazonamide melting at 104° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(CC1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC)=O;m1_m2_m3:[OH-].[Na+], Reagents are:m1_m2_m3:C(C)O, and Products are 0:COC1=CC=C(C=C1)C=1N(C(=NN1)CC(=O)O)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4 g of the product of Example 16, 10 ml of 2N sodium hydroxide and 20 ml of ethanol was stirred at 60° C. under argon for 30 minutes and the ethanol was evaporated at 40° C. under reduced pressure. 9.9 ml of 2N hydrochloric acid were added to the aqueous solution and the mixture stood at 0° to 5° C. for 16 hours and was filtered. The recovered product was cmpasted several times with ice water to remove chlorides and was dried at room temperature under reduced pressure of 0.5 to 1 mmHg to obtain 3.6 g of 5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole-3-acetic acid. |
Here is a chemical reaction formula: Reactants are:m3:O.NN;m4:O;m1_m2:CN(C1=CC=C(C=C1)C(NC1=CC=C(C=C1)[N+](=O)[O-])=S)C;m1_m2:C(C)O, Reagents are:, and Products are 0:CN(C1=CC=C(C=C1)C(N)=NNC1=CC=C(C=C1)[N+](=O)[O-])C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 30 g of the product of Step A and 180 ml of ethanol was heated to reflux and 30 ml of hydrazine hydrate were added thereto. The mixture was refluxed for 15 minutes and then 180 ml of distilled water were added thereto. The mixture was cooled to 10° C. and was vacuum filtered. The product was washed with water and dried to obtain 19 g of 4-dimethylamino-N'-(4-nitrophenyl)-benzenecarbohydrazonamide melting at 174° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)OC, Reagents are:m1_m2:Br, and Products are 0:C(C)C1=NN=C(N1C1=CC=CC=C1)C1=CC=C(C=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.86 g of 3-ethyl-5-(4-methoxyphenyl)-4-phenyl-4H-1,2,4-triazole and 20 ml of a hydrobromic acid solution at 48% was refluxed with stirring for one hour and the mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 20 ml of hot water and ammonium hydroxide was added until the pH was alkaline. The mixture was stood overnight with stirring and was vacuum. The product was washed with water and dried at 90° C. under reduced pressure. The 3.65 g of product were crystallized from methanol and the mixture was iced and vacuum filtered. The crystals were washed by empasting with methanol and were dried at 90° C. under reduced pressure to obtain 3.245 g of 4-(3-ethyl-4-phenyl-4H-1,2,4-triazol-5-yl)-phenol melting at 275° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrCCCCOC1=C(C=O)C=C(C=C1)S(=O)(=O)C;m1_m2_m3_m4:C(CC(=O)C)(=O)OC;m1_m2_m3_m4:COC(\C=C(\C)/N)=O, Reagents are:m1_m2_m3_m4:C(C)(C)O, and Products are 0:BrCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.6 g of 2-(4-bromobutoxy)-5-methylsulfonylbenzaldehyde, 2.6 g of methyl acetoacetate and 2.9 g of 3-aminocrotonic acid methyl ester were dissolved in 16 ml of isopropanol, and the solution was heated for 5 hours. After cooling, precipitated crystals were collected by filtration, and recrystallized from methanol to give 6.3 g of dimethyl 4-[2(4-bromobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C1(C=2C(C(N1CCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)=O)=CC=CC2)=O;m1_m2_m3:O.NN, Reagents are:m1_m2_m3:C(C)O, and Products are 0:NCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 6.9 g of dimethyl 4-[2-(4-phthalimidobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 5.9 g of hydrazine monohydrate in 170 ml of % ethanol(water: 5%) was refluxed under heating for 6 hours. After cooling, the reaction solution was concentrated under reduced pressure. The residue was extracted with chloroform, and the extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Crude crystals thus obtained were recrystallized from chloroform-ether to give 2.6 g of dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m5_m1_m2_m3_m4:ClCCCCOC1=C(C=O)C=C(C=C1)[N+](=O)[O-];m5_m1_m2_m3_m4:C(CC)(=O)CC(=O)OCC;m5_m1_m2_m3_m4:N1CCCCC1;m5_m1_m2_m3_m4:C(C)(=O)O;m5_m1_m2_m3_m4:C1=CC=CC=C1, Reagents are:, and Products are 0:C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCCl)C(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 106 ml of dry benzene were dissolved 13.0 g of 2-(4-chlorobutoxy)-5-nitrobenzaldehyde, 7.28 g of ethyl propionylacetate, 0.20 ml of piperidine and 0.62 ml of acetic acid, and the solution was refluxed for 9 hours while removing water using a Dean-Stark trap. After cooling the reaction solution, 6.52 g of ethyl 3-aminocrotonate was added to the solution, and the mixture was refluxed under heating for 11 hours. After cooling the mixture, precipitated crude crystals were collected by filtration, and recrystallized from methanol to give 13.13 g of diethyl 2-ethyl-4-[2-(4-chlorobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCN1C(C=2C(C1=O)=CC=CC2)=O)C(=O)OCC)C;m1_m2_m3:O.NN, Reagents are:m1_m2_m3:C(C)O, and Products are 0:NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)CC)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 12.4 g of diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 10.4 g of hydrazine monohydrate in 270 ml of 95% ethanol (water: 5%) was refluxed under heating for 10 hours. After cooling the reaction solution, the solution was concentrated under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Crude crystals thus obtained were recrystallized from chloroform-ether to give 6.4 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC;m3_m1_m2:C1C(C2=CC=CC=C2)O1, Reagents are:m3_m1_m2:CN(C=O)C, and Products are 0:OC(CNCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 30 ml of N,N-dimethylformamide were dissolved 2 g of dimethyl 4-[2-(2-aminoethoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.6 g of styrene oxide, and the solution thus formed was allowed to stand for 2 days at room temperature. The reaction solution was concentrated under reduced pressure, and the residue was subjected to silica gel column chromatography. The product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethyl acetate to give 500 mg of dimethyl 4-[2-[2-(β-hydroxyphenethylamino)ethoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC;m3_m1_m2:C1(=CC=CC=C1)OCC1CO1, Reagents are:m3_m1_m2:CO, and Products are 0:OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 1,300 ml of methanol were dissolved 13 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 4.5 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (96:4 v/v). Crude crystals were recrystallized from ethanol to give 9 g of dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC;m3_m1_m2:C1(=CC=CC=C1)OCC1CO1, Reagents are:m3_m1_m2:CO, and Products are 0:OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)C)C(=O)OCC)COC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 500 ml of methanol were dissolved 5.2 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.7 g of glycidyl phenyl ether, and the solution thus formed was refluxed under heating for 16 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chlroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol to give 2.2 g of diethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |