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Here is a chemical reaction formula: Reactants are:m2_m5:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)NC(=N3)C)C=C1;m4_m7:O;m3:CI;m1:[H-].[Na+], Reagents are:m2_m5:CN(C=O)C;m6:CN(C=O)C;m4_m7:C(Cl)(Cl)Cl, and Products are 0:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a stream of argon, 144 mg of 60% sodium hydride was suspended in a small volume of N,N-dimethylformamide to which, with cooling on an ice bath, was then added dropwise a solution prepared by dissolving 500 mg of 6-(4-nitrobenzoyl)-2-methyl-1,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine in 20 ml of N,N-dimethylformamide. After 1 hour of stirring at room temperature, the reaction solution was mixed with 0.11 ml of methyl iodide and stirred for 24 hours at room temperature. The reaction solution was mixed with water and chloroform, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography to obtain 351 mg of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine from the chloroform-methyl alcohol (30:1) eluate. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1, Reagents are:m1_m2:CO;m3:[C].[Pd], and Products are 0:NC1=CC=C(C(=O)N2CCC3=C(C4=C2C=CC=C4)N=C(N3C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 1.421 g portion of 6-(4-nitrobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine was dissolved in 50 ml of methyl alcohol, and the solution was mixed with 300 mg of palladium-carbon and subjected to hydrogenation under normal pressure. After completion of the hydrogen absorption, the reaction mixture was subjected to filtration and the resulting filtrate was concentrated to obtain 571 mg of 6-(4-aminobenzoyl)-2,3-dimethyl-3,4,5,6-tetrahydroimidazo[4,5-d][1]benzazepine. |
Here is a chemical reaction formula: Reactants are:m2_m3:BrC=1C=C(C=CC1)CC(=O)OCC;m2_m3:BrC=1C=C(C=CC1)CC(=O)OCC;m4:[H-].C(C(C)C)[Al+]CC(C)C;m1:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, Reagents are:, and Products are 0:BrC=1C=C(C=CC1)CC=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Compound G can be obtained as described in J. Med. Chem. 1995, 38, 4764-4767, and as shown in Reaction Scheme 1. Thus, referring now specifically to Reaction Scheme 1, ethyl 3-bromophenylacetate (Compound B, made by esterification of 3-bromophenylacetic acid) is reduced with diisobutylaluminum hydride (DIBAL H) to yield (3-bromophenyl)acetaldehyde. (3-Bromophenyl)acetaldehyde is reacted in a Wittig reaction with (carbethoxymethylene)triphenylphosphorane to provide a mixture of E and Z ethyl 4-(3-bromophenyl)but-2-enoates. The latter compounds are hydrogenated to yield ethyl 4-(3-bromophenyl)butanoate (Compound D). Compound D is reacted with the Grignard reagent derived from methylbromide to give the tertiary alcohol 5-(3-bromophenyl)-2-methylpentan-2-ol (Compound E) (It should be apparent to those skilled in the art, that the choice of the Grignard reagent used in this reaction step determines the nature of the R1 substituent in the resulting compounds of the invention.) Compound E is then treated with acid to cyclize it and to form 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F). Compound F is oxidized with chromium trioxide to yield 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G). The isomeric compound, 6-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound H) can be obtained, starting with ethyl (4-bromophenyl)acetate, in accordance with the sequence of reactions illustrated in Reaction Scheme 1 for Compound G. |
Here is a chemical reaction formula: Reactants are:m1:BrC=1C=C2C(CCC(C2=CC1)(C)C)O;m2:[Si](C)(C)(C(C)(C)C)Cl, Reagents are:, and Products are 0:BrC=1C=C2C(CCC(C2=CC1)(C)C)O[Si](C)(C)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Continuing on with the description of Reaction Scheme 6, 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene is reacted in the presence of base with t-butyldimethylsilyl chloride to provide 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-(t-butyldimethylsilyloxy)naphthalene (Compound B15). The starting 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene can be obtained by reduction of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G). Under conditions similar to the ones described above Compound B15 is converted to the boronic acid derivative (5,5-dimethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-naphth-2-yl)boronic acid (Compound B14). Compound B14 is then coupled with ethyl 6-bromo-naphthalene-2-carboxylate to yield ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-2-yl]naphth-2-oate (Compound B3). Compound B3 is then reacted with tetrabutylammonium fluoride to remove the t-butyldimethylsilyl blocking group and to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-2-yl]naphth-2-oate (Compound B4). Compound B4 can be acylated to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(O-acetyl)-naphth-2-yl]naphth-2-oate (Compound B10), or methoxymethylated with methoxymethyl chloride in the presence of base (preferably ethyl N,N-diisopropylamine, Hunig's base) to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(methoxymethyloxy)-naphth-2-yl]naphth-2-oate (Compound B8), and oxidized with N-methyl morpholine N-oxide to provide ethyl -6-[5,5-dimethyl-5,6-dihydro-naphthlen-8(7H)-one-2-yl]-naphthalen-2-oate (Compound B6). Compounds B8 and B10 of the invention are within the scope of Formula 1, whereas Compound B6 is within the scope of Formula 2. Compound B6 can be converted into the O-methyloxime (ethyl 6-[5,5-dimethyl-5,6-dihydro-naphthlen-8(7H)-anti-(O-methyl-oxime)-2-yl]-naphthalen-2-oate (Compound B11) not shown in the scheme) and into other derivatives such as oximes, imines, hydrazones and the like, as is described above in connection with Reaction Scheme 2. Further derivatives of Compound B6 (and of analogous compounds) wherein the 8-oxo function of the molecule is modified can be obtained in accordance with the general synthetic methodology described in this specification. For example the trifluoromethylsulfonyl (triflate) derivative can be obtained in analogy to the reaction leading to Compound A9 as described in Reaction Scheme 2, and the trifluoromethylsulfonyl (triflate) derivative is reacted with the reagents R14Me to provide compounds of Formula 6. ##STR21## |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1(C=2C=CC(=CC2C(CC1)O[Si](C)(C)C(C)(C)C)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C;m1_m2:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, Reagents are:, and Products are 0:CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Continuing on with the description of Reaction Scheme 6, 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene is reacted in the presence of base with t-butyldimethylsilyl chloride to provide 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-(t-butyldimethylsilyloxy)naphthalene (Compound B15). The starting 6-bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-hydroxynaphthalene can be obtained by reduction of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G). Under conditions similar to the ones described above Compound B15 is converted to the boronic acid derivative (5,5-dimethyl-8-(t-butyldimethylsilyloxy)-5,6,7,8-tetrahydro-naphth-2-yl)boronic acid (Compound B14). Compound B14 is then coupled with ethyl 6-bromo-naphthalene-2-carboxylate to yield ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-2-yl]naphth-2-oate (Compound B3). Compound B3 is then reacted with tetrabutylammonium fluoride to remove the t-butyldimethylsilyl blocking group and to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-2-yl]naphth-2-oate (Compound B4). Compound B4 can be acylated to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(O-acetyl)-naphth-2-yl]naphth-2-oate (Compound B10), or methoxymethylated with methoxymethyl chloride in the presence of base (preferably ethyl N,N-diisopropylamine, Hunig's base) to give ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(methoxymethyloxy)-naphth-2-yl]naphth-2-oate (Compound B8), and oxidized with N-methyl morpholine N-oxide to provide ethyl -6-[5,5-dimethyl-5,6-dihydro-naphthlen-8(7H)-one-2-yl]-naphthalen-2-oate (Compound B6). Compounds B8 and B10 of the invention are within the scope of Formula 1, whereas Compound B6 is within the scope of Formula 2. Compound B6 can be converted into the O-methyloxime (ethyl 6-[5,5-dimethyl-5,6-dihydro-naphthlen-8(7H)-anti-(O-methyl-oxime)-2-yl]-naphthalen-2-oate (Compound B11) not shown in the scheme) and into other derivatives such as oximes, imines, hydrazones and the like, as is described above in connection with Reaction Scheme 2. Further derivatives of Compound B6 (and of analogous compounds) wherein the 8-oxo function of the molecule is modified can be obtained in accordance with the general synthetic methodology described in this specification. For example the trifluoromethylsulfonyl (triflate) derivative can be obtained in analogy to the reaction leading to Compound A9 as described in Reaction Scheme 2, and the trifluoromethylsulfonyl (triflate) derivative is reacted with the reagents R14Me to provide compounds of Formula 6. ##STR21## |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)OC(CC1=CC=C(C=C1)Br)=O;m1_m2_m3:C(C)OC(CC1=CC=C(C=C1)Br)=O;m1_m2_m3:BrC=1C=C(C=CC1)CC(=O)O, Reagents are:, and Products are 0:C(C)OC(CC1=CC(=CC=C1)Br)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing the same general procedure as for the preparation of ethyl(4-bromophenyl)acetate (Compound A), 100 g (463 mmol) of 3-bromophenylacetic acid was converted into the title compound (yellow oil) using 2 g of conc. H2SO4 and 500 ml of ethanol. PMR (CDCl3): δ 1.26 (3H, t, J=7.0 Hz), 3.56 (2H, s), 4.16 (2H, q, J=7.0 Hz), 7.16-7.26 (2H, m), 7.38-7.46 (2H, m). |
Here is a chemical reaction formula: Reactants are:m4:[H-].C(C(C)C)[Al+]CC(C)C;m1_m2_m5_m3:C(C)OC(CC1=CC=C(C=C1)Br)=O;m1_m2_m5_m3:C(C)OC(CC1=CC=C(C=C1)Br)=O;m1_m2_m5_m3:[H-].C(C(C)C)[Al+]CC(C)C, Reagents are:m1_m2_m5_m3:C(Cl)Cl, and Products are 0:BrC1=CC=C(C=C1)CC=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl(4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an additional hour. The reaction was quenched by the dropwise addition of methanol (10 ml), followed by water (10 ml) and 10% HCl (40 ml). The mixture was then warmed to 0° C., stirred for 10 minutes and then washed with water (15 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgSO4 and the solvent distilled off at ambient temperature to give crude (4-bromophenyl)acetaldehyde. To a cold solution (0° C.) of this crude aldehyde in 150 ml of CH2 Cl2 was added a solution of 26 g (74.6 mmol) of (carbethoxymethylene)triphenylphosphorane in 50 ml of CH2Cl2. The mixture was stirred for 16 hours, concentrated in vacuo and purified by flash chromatography (silica, 10% EtOAc-hexane) to give ethyl 4-(4-bromophenyl)but-2-enoate as a mixture of E:Z isomers. This isomeric mixture was dissolved in 150 ml of EtOAc and hydrogenated over 1 g of 10% Pd/C for 6 hours. The catalyst was filtered off and the filtrate concentrated in vacuo to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC1=CC=C(C=C1)CC=O;m1_m2_m3_m4:ClCl;m1_m2_m3_m4:C(=O)(OCC)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m1_m2_m3_m4:C(Cl)Cl, and Products are 0:BrC1=CC=C(C=C1)CC=CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution (-78° C.) of 15 g (62 mmol) of ethyl(4-bromophenyl)acetate (Compound A) in 150 ml of CH2Cl2 was added dropwise (over a span of 1 hour) 65 ml (65 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M solution in hexane). After the DIBAL-H addition was complete, the reaction was stirred at -78° C. for an additional hour. The reaction was quenched by the dropwise addition of methanol (10 ml), followed by water (10 ml) and 10% HCl (40 ml). The mixture was then warmed to 0° C., stirred for 10 minutes and then washed with water (15 ml), 10% aqueous NaHCO3 (10 ml) and brine (10 ml). The organic phase was dried over MgSO4 and the solvent distilled off at ambient temperature to give crude (4-bromophenyl)acetaldehyde. To a cold solution (0° C.) of this crude aldehyde in 150 ml of CH2 Cl2 was added a solution of 26 g (74.6 mmol) of (carbethoxymethylene)triphenylphosphorane in 50 ml of CH2Cl2. The mixture was stirred for 16 hours, concentrated in vacuo and purified by flash chromatography (silica, 10% EtOAc-hexane) to give ethyl 4-(4-bromophenyl)but-2-enoate as a mixture of E:Z isomers. This isomeric mixture was dissolved in 150 ml of EtOAc and hydrogenated over 1 g of 10% Pd/C for 6 hours. The catalyst was filtered off and the filtrate concentrated in vacuo to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)OC(CCCC1=CC=C(C=C1)Br)=O;m1_m2_m3_m4:C(C)OC(CCCC1=CC=C(C=C1)Br)=O;m1_m2_m3_m4:BrC=1C=C(C=CC1)CC(=O)OCC;m1_m2_m3_m4:BrC=1C=C(C=CC1)CC(=O)OCC, Reagents are:, and Products are 0:BrC=1C=C(C=CC1)CCCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing the same general multistep preparation as for ethyl4-(4-bromophenyl)butanoate (Compound C), 60 g (246 mmol) of ethyl (3-bromophenyl)acetate (Compound B) was converted into the title compound (oil) using 255 ml (255 mmol) of diisobutylaluminum hydride (DIBAL-H, 1M in hexane), 85.8 g (250 mmol) of (carbethoxymethylene)triphenylphosphorane and 1.7 g of 10% Pd/C. |
Here is a chemical reaction formula: Reactants are:m6_m1_m2_m3_m4_m5:C(C)(=O)OC(C)=O;m6_m1_m2_m3_m4_m5:C(C)(=O)O;m6_m1_m2_m3_m4_m5:BrC=1C=C2CCCC(C2=CC1)(C)C;m6_m1_m2_m3_m4_m5:BrC=1C=C2CCCC(C2=CC1)(C)C, Reagents are:m6_m1_m2_m3_m4_m5:C1=CC=CC=C1;m6_m1_m2_m3_m4_m5:[O-2].[O-2].[O-2].[Cr+6], and Products are 0:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold mixture (0° C.) of 209 g (200 mmol) of chromium trioxide, 100 ml (1.06 mol) of acetic anhydride and 200 ml (3.5 mol) of acetic acid was added a solution of 10 g (41.8 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound F) in 125 ml of benzene. The reaction mixture was stirred for 1 hour, quenched with ice cold water and extracted with Et2O (3×100 ml). The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (silica, 10% EtOAc-hexane) to give the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m5:[NH4+].[Cl-];m1_m6_m2:S1C=NC=C1;m1_m6_m2:C(CCC)[Li];m3_m4_m10_m8:CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C;m3_m4_m10_m8:CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)/C=C/C1=CC=C(C(=O)OCC)C=C1)C, Reagents are:m9_m7:O1CCCC1;m9_m7:[Cl-].[Zn+2].[Cl-];m1_m6_m2:C1CCOC1;m3_m4_m10_m8:O1CCCC1;m3_m4_m10_m8:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1, and Products are 0:CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CN1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of thiazole (0.38 g (0.10 mL, 1.4 mmol) in THF (2.0 mL) was added n-butyl lithium (1.6M solution in hexanes, 0.5 mL, 0.8 mmol) and stirred for 30 min. To this solution was added 0.176 g (1.3 mmol) of zinc chloride in 3.0 mL of tetrahydrofuran and stirred for 45 min. The resulting turbid solution was transferred, via cannula, to a flask containing a mixture of 0.17 g (0.35 mmol) of ethyl (E)-4-[2-(5,5-dimethyl-8-(trifluoromethylsulfonyl)oxy-5,6-dihydronaphthalen-2-yl)ethenyl]benzoate (Compound A9) and 15 mg (0.01 mmol) of tetrakis(triphenylphosphine)palladium(0) in 3.0 mL of tetrahydrofuran. The reaction mixture was stirred for 1 h at ambient temperature and 1.5 h at 55° C. The reaction mixture was treated with aqueous NH4Cl, and extracted with EtOAc (2×). The combined organic layer was washed with brine and dried (MgSO4). The solvent was removed under reduced pressure and the crude product was purified by flash chromatography (silica, 20% ethyl acetate in hexane) to afford the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:BrC1=CC=2C(=CCC(C2C=C1)(C)C)SC1=CC=CC=C1;m1_m2_m4_m3:C(=C)C1=CC=C(C(=O)OCC)C=C1;m1_m2_m4_m3:C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C, Reagents are:m1_m2_m4_m3:C(C)N(CC)CC;m5:C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-], and Products are 0:CC1(C=2C=CC=C(C2C(=CC1)SC1=CC=CC=C1)/C=C/C1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a degassed solution of 0.35 g (1.0 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(phenylthio)-naphthalene (Compound A35) and 0.34 g (1.9 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 0.066 g (0.2 mmol) of tri-o-tolylphosphine and then 0.025 g (0.1 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo. The residue was purified by flash chromatography (silica, 5% ethyl acetate in hexane), followed by recrystallization using EtOH to afford the title compound as white crystals. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:BrC1=CC=2C(=CCC(C2C=C1)(C)C)SCC;m1_m2_m4_m3:C(=C)C1=CC=C(C(=O)OCC)C=C1;m1_m2_m4_m3:C1(=C(C=CC=C1)P(C1=C(C=CC=C1)C)C1=C(C=CC=C1)C)C, Reagents are:m5:C(C)(=O)[O-].[Pd+2].C(C)(=O)[O-];m1_m2_m4_m3:C(C)N(CC)CC, and Products are 0:CC1(C=2C=CC(=CC2C(=CC1)SCC)/C=C/C1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a degassed solution of 0.50 g (1.7 mmol) of 2-bromo-5,6-dihydro-5,5-dimethyl-8-(ethylthio)-naphthalene (Compound A36) and 0.45 g (2.5 mmol) of ethyl 4-vinylbenzoate in 4.0 mL of triethylamine, was added 109 mg (0.36 mmol) of tri-o-tolylphosphine and then 35 mg (0.16 mmol) of palladium(II) acetate. The reaction was heated at 90° C. for 2.25 h. The reaction was concentrated in vacuo and purified by flash chromatography (silica, 2% ethyl acetate in hexane) to afford the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m3:BrCC(=O)OCC;m6_m4_m1_m2_m5:CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C;m6_m4_m1_m2_m5:CC1(C=2C=CC(=CC2C(CC1)=O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C;m6_m4_m1_m2_m5:C1=CC=CC=C1;m6_m4_m1_m2_m5:C1=CC=CC=C1, Reagents are:m6_m4_m1_m2_m5:[Zn], and Products are 0:CC1(C=2C=CC(=CC2C(CC1)(C(=O)OCCC)O)/C=C/C1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a refluxing solution of 0.75 g (11.5 mmol) of granular zinc in 5.0 mL of benzene was added a solution of ethyl(E)-4-[2-(5,5-dimethyl-5,6,-dihydro-naphthalen-8(7H)-one-2-yl)ethenyl]-benzoate (Compound A2) in 5.0 mL of benzene followed by 0.27 g (0.18 mmol) of ethyl bromoacetate. The resulting mixture was refluxed for 24 h. The reaction was cooled, filtered through celite. The filtrate was washed with 10% HCl, sat. aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica, 10% ethyl acetate in hexane) to afford the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m7_m3:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m1_m2_m7_m3:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m1_m2_m7_m3:C1CCOC1;m4_m5_m6:C1(=CC=CC=C1)S;m4_m5_m6:C(C)N(CC)CC;m4_m5_m6:C1CCOC1, Reagents are:m1_m2_m7_m3:[Ti](Cl)(Cl)(Cl)Cl;m8:O, and Products are 0:CC1(CC=C(C2=CC(=CC=C12)Br)SC1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G, 1.48 g, 5.9 mmol), titanium tetrachloride (1.09 g, 5.7 mmol) and THF (10 mL) was added a mixture of thiophenol (660 mg, 6 mmol), triethylamine (1.16 g, 11.5 mmol) and THF (20 mL) via an addition funnel at ambient temperature. The mixture was stirred for 5 h, and water (10 mL) was added, extracted with ether (3×50 mL). The combined organic layer was washed successively with water (10 mL), 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried (MgSO4) and the solvent distilled off at reduced pressure. After silicagel chromatography the title compound was obtained as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m8:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m1_m2_m5_m8:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m3_m4_m6:C(C)S;m3_m4_m6:C(C)N(CC)CC, Reagents are:m1_m2_m5_m8:O1CCCC1;m1_m2_m5_m8:[Ti](Cl)(Cl)(Cl)Cl;m3_m4_m6:O1CCCC1;m7:O, and Products are 0:BrC1=CC=2C(=CCC(C2C=C1)(C)C)SCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.03 g (4.1 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) in 30.0 mL of tetrahydrofuran, was added dropwise 0.49 g (0.85 mL, 7.8 mmol) of titaniumtetrachloride and the resulting solution stirred for 10 min. A solution of 35 mg (0.50 mL, 6.7 mmol) of ethanethiol and 0.54 g (0.75 mL, 5.4 mmol) of triethylamine in 10.0 mL of tetrahydrofuran was added and the reaction stirred at room temperature for 13 h. The mixture was diluted with water and extracted with ether (2×). The organic phase was washed with brine, dried over Na2SO4 and then concentrated in vacuo. Purification by flash chromatography (silica, 100% hexane) gave the title compound as an off. |
Here is a chemical reaction formula: Reactants are:m4:COCCl;m6:O;m1_m2_m7_m3:CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C;m1_m2_m7_m3:CC1(C=2C=CC(=CC2C(CC1)O)C=1C=C2C=CC(=CC2=CC1)C(=O)OCC)C;m1_m2_m7_m3:CCN(C(C)C)C(C)C;m5:[I-].C(C)(C)(C)[NH3+], Reagents are:m0_m8:C(C)(=O)OCC;m1_m2_m7_m3:C(Cl)Cl, and Products are 0:C(C)OC(=O)C1=CC2=CC=C(C=C2C=C1)C1CC(C=2C=CC=CC2C1OCOC)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (0° C.) solution of 130 mg (0.35 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(hydroxy)-naphth-7-yl]naphth-2-oate (Compound B4) in 2.0 mL of methylene chloride was added 50 mg (0.15 mL, 0.86 mmol) of Hunig's base, followed by 0.21 g (0.20 mL, 2.6 mmol) chloromethyl methyl ether was added and stirred at room temperature for 14 h. About 500 mgs of t-butylammonium iodide was then added and the reaction was warmed to 35° C. for one additional hour. The reaction was diluted with water, and extracted with CH2Cl2 (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an off. The title compound was obtained as an oil after flash chromatography (silica, 10% ethyl acetate). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:BrC=1C=C2CCCC(C2=CC1)(C)C;m1_m4_m2:[Li]CCCC;m3:C(C)(C)OB(OC(C)C)OC(C)C, Reagents are:m1_m4_m2:C1(=CC=CC=C1)C;m5:Cl, and Products are 0:CC1(C=2C=CC(=CC2CCC1)B(O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold (-78° C.) solution of 2.02 g (8.4 mmol) of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene in 11.0 mL of toluene, was added 4.6 g (6.8 mL, 10.9 mmol, 1.6M in hexane) of n-BuLi. The resulting solution was stirred at -78° C. for 45 min. and then 2.40 g (3.0 mL, 12.7 mmol) of triisopropylborate was dropwise added and the reaction stirred at room temperature for 12 h. The reaction was then diluted with 10% HCl, and extracted with ether (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Recrystallization from hexane afforded the title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5_m4:CC1(C=2C=CC(=CC2C(CC1)(CC(=O)OCC)O)N=NC1=CC=C(C(=O)OCC)C=C1)C;m1_m2_m3_m5_m4:CC1(C=2C=CC(=CC2C(CC1)(CC(=O)OCC)O)N=NC1=CC=C(C(=O)OCC)C=C1)C;m1_m2_m3_m5_m4:C1CCC(CC1)N=C=NC2CCCCC2, Reagents are:m1_m2_m3_m5_m4:C1=CC=CC=C1;m1_m2_m3_m5_m4:Cl[Cu], and Products are 0:CC1(C=2C=CC(=CC2C(=CC1)CC(=O)OCC)N=NC1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of (±)ethyl 4-[(5,5-dimethyl-8-hydroxy-8-carbethoxymethyl-5,6,7,8-tetrahydronaphth-2-yl)azo]benzoate (Compound D1, 108 mg, 0.25 mmol), DCC (55.9 mg, 0.271 mmol) and CuCl (36.6 mg, 0.37 mmol) in 8 ml of dry benzene was heated under reflux for 7 days. After cooling to room temperature, the solids were filtered out and the solution was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over Na2 SO4. The solvent was removed under reduced pressure, the crude material was purified by flash chromatography (silicagel, 10% ethyl acetate in hexane) to afford the pure title compounds as red oils. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC1(CCC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C;m1_m2_m3_m4:CC1(CCC(C2=CC(=CC=C12)[N+](=O)[O-])=O)C, Reagents are:m1_m2_m3_m4:CCOC(=O)C;m1_m2_m3_m4:[Pd], and Products are 0:CC1(CCC(C2=CC(=CC=C12)N)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 230.0 mg (1.05 mmol) 3,4-dihydro-4,4-dimethyl-7-nitro-naphthalen-1(2H)-one (Compound D8) in 5.0 mL of EtOAc was stirred at room temperature with a catalytic amount of 10% Pd-C under 1 atm of H2 for 24 h. The catalyst was removed by filtration through a pad of Celite, and the filtrate concentrated under reduced pressure to give the title compound as a dark green oil. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2:S1C=CC=C1;m1_m4_m2:[Li]C(C)(C)C;m3_m9_m6:CC1(C=2C=CC(=CC2C(=CC1)OS(=O)(=O)C(F)(F)F)N=NC1=CC=C(C(=O)OCC)C=C1)C, Reagents are:m1_m4_m2:C1CCOC1;m8_m5:C1CCOC1;m8_m5:[Cl-].[Cl-].[Zn+2];m7:[NH4+].[Cl-];m3_m9_m6:C1CCOC1;m3_m9_m6:C=1C=CC(=CC1)[P](C=2C=CC=CC2)(C=3C=CC=CC3)[Pd]([P](C=4C=CC=CC4)(C=5C=CC=CC5)C=6C=CC=CC6)([P](C=7C=CC=CC7)(C=8C=CC=CC8)C=9C=CC=CC9)[P](C=1C=CC=CC1)(C=1C=CC=CC1)C=1C=CC=CC1, and Products are 0:CC1(C=2C=CC(=CC2C(=CC1)C=1SC=CC1)N=NC1=CC=C(C(=O)OCC)C=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cold solution (-78° C.) of thiophene (0.07 ml, 0.75 mmol) in 1.5 ml of THF was added t-BuLi (0.457 ml, 0.75 mmol, 1.7M in pentane) and stirred for 2 h. To this solution, ZnCl2 (168 mg, 1.2 mmol) in 1.5 ml of THF was added. The resulting solution was warmed to room temperature, stirred for 1 h and was added (via cannula) to a solution of ethyl 4-[(5,6-dihydro-5,5-dimethyl-8-trifluoromethylsulfonyloxy-naphthalen-2-yl)azo]benzoate (Compound D11, 150 mg, 0.30 mmol) and tetrakis(triphenylphosphine)palladium(0) (10.6 mg) in 2.5 ml of THF. The resulting mixture was heated at 50° C. for 2.5 h. The reaction was diluted with sat. aqueous NH4Cl and extracted with ethyl acetate. The combined organic layer was dried over Na2SO4 and concentrated to an oil. The crude product was purified by flash chromatography (silica, ethyl acetate:hexane 5:95) to afford the title compound as a red foam. |
Here is a chemical reaction formula: Reactants are:m3:O;m1_m2_m4:CC1(OCCO1)C=1C=C2C(CCC(C2=CC1)(CC(=O)OCC)O)(C)C;m1_m2_m4:CC=1C=CC(=CC1)S(=O)(=O)O, Reagents are:m1_m2_m4:C1=CC=CC=C1, and Products are 0:CC1(CC=C(C2=CC=C(C=C12)C(C)=O)CC(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of (±)6-(2-methyl-1,3-dioxolan-2-yl)-1,2,3,4-tetrahydro-4,4-dimethyl-1-hydroxy-1-(carboethoxymethyl)-naphthlene ((Compound D16, 321 mg, 0.90 mmol) and catalytic amount of TsOH in 20 ml of benzene was refluxed for 12 h. During the reaction the water generated from the reaction was periodically removed by a Dean-Stark trap. The solvent was removed and the residue was purified by column chromatography (silica, ethyl acetate/hexane (1/3)) to give the title compound as an oil (215 mg). |
Here is a chemical reaction formula: Reactants are:m3:O=S(Cl)Cl;m1_m4_m2:CC1(CCC(C2=CC=CC=C12)=O)C;m1_m4_m2:[Li]C(C)(C)C;m1_m4_m2:CCOCC, Reagents are:, and Products are 0:CC1(CC=C(C2=CC=C(C=C12)C(C)=O)C(C)(C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(2-methyl-1,3-dioxolan-2-yl)!-3,4-dihydro-4,4-dimethylnaphthlen-1(2H)-one ((Compound D15, 353 mg, 1.36 mmol) in 3 ml of dry ether at -78° C. was added dropwise t-BuLi (1 ml, 1.7 mmol, 1.7M solution in pentane). This dear light yellow solution was left at -78° C. for 30 min. Then, fleshly distilled SOCl2 (0.15 ml, 2.0 mmol) was added. The reaction mixture was stirred at -78° C. for additional 30 min and thereafter slowly warmed to room temperature. The reaction was quenched by addition of saturated NH4Cl. The white solids were removed by filtration and the clear solution was concentrated to an oil, and purified by column chromatography with ethyl acetate/hexane (1/10) to give the title compound as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:S1C(=CC=C1)C1=CCC(C2=CC(=CC=C12)C(C)=O)(C)C;m1_m4_m2_m3:C(=O)(O)C1=CC=C(C=O)C=C1;m1_m4_m2_m3:[OH-].[Na+], Reagents are:m1_m4_m2_m3:CO, and Products are 0:O=C(C=CC1=CC=C(C(=O)O)C=C1)C1=CC=2C(CC=C(C2C=C1)C=1SC=CC1)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 62.6 mg (0.222 mmol) 3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene (Compound D33) in 4.0 mL of MeOH were added 33.4 mg (0.222 mmol) of 4-carboxy benzaldehyde, and 240.0 mg (6.00 mmol; 2.0 mL of 3M aqueous NaOH). The resulting solution was stirred at room temperature for 12 h, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer washed with H2O, and saturated aqueous NaCl, before being dried over Na2 SO4. Removal of the solvents under reduced pressure gave the title compound as a pale green solid after recrystallization from EtOH. |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m5_m6_m3:CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C;m1_m2_m5_m6_m3:CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C;m1_m2_m5_m6_m3:[OH-].[Na+], Reagents are:m1_m2_m5_m6_m3:C(C)O;m1_m2_m5_m6_m3:C1CCOC1, and Products are 0:CC1(C=2C=CC=CC2C(CC1)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 1.05 g, 4.5 mmol) in 10 mL of ethanol and THF (10 mL) was added sodiumhydroxide 9 mL (1M solution). The solution was stirred for 16 h and thereafter acidified with 10% HCl. The mixture was extracted with ethyl acetate, the combined organic layer was washed with water and brine, and dried over MgSO4. The solvent was distilled off under reduced pressure to afford the title compound as a white solid. 1H NMR (Acetone-D6): δ 1.44 (s, 6H), 2.07 (t, J=6.7 Hz, 2H), 2.73 (t, J=6.7 Hz, 2H), 7.70 (d, J=8.2 Hz, 1H), 8.19 (dd, J=1.9, 8.2 Hz, 1H), 8.57 (d, J=1.9 Hz, 1H). |
Here is a chemical reaction formula: Reactants are:m5:O;m1_m2_m6_m8:CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C;m1_m2_m6_m8:CC1(C=2C=CC(=CC2C(CC1)=O)C(=O)OC)C;m3_m4_m7:C1(=CC=CC=C1)S;m3_m4_m7:CCN(CC)CC, Reagents are:m1_m2_m6_m8:C1CCOC1;m1_m2_m6_m8:Cl[Ti](Cl)(Cl)Cl;m3_m4_m7:C1CCOC1, and Products are 0:COC(=O)C1=CC=2C(=CCC(C2C=C1)(C)C)SC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 835.0 mg, 3.60 mmol) in 25.0 mL of THF at room temperature was added TiCl4 (670.0 mg, 3.55 mmol). Thereafter a solution of thiophenol (430.0 mg, 3.90 mmol) and Et3N (730.0 mg, 7.20 mmol) in 10 mL THF was added. The resulting brown mixture was stirred for 6 h before H2O was carefully added to quench the reaction. The product was extracted into Et2O and the combined organic layers washed with saturated aqueous NaCl and dried over MgSO4. Removal of the solvents under reduced pressure afforded a solid from which the title compound was isolated as a yellow solid by column chromatography (5% EtOAc-hexanes). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:BrCC(=O)OCC;m1_m2_m3_m5:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C;m1_m2_m3_m5:BrC1=CC=C2C(CCC(C2=C1)=O)(C)C, Reagents are:m6_m4:C1=CC=CC=C1;m6_m4:[Zn];m1_m2_m3_m5:C1=CC=CC=C1, and Products are 0:OC1(CCC(C2=CC=C(C=C12)Br)(C)C)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of Zn (1.20 g, 18.4 mmol) in 10 mL benzene at 100° C. was slowly added a solution of ethyl 2-bromoacetate (658.0 mg, 3.94 mmol) and 3,4-dihydro-4,4-dimethyl-7-bromo-naphthalen-1(2H)-one (Compound G, 500.0 mg, 1.97 mmol) in 20.0 mL benzene. The resulting mixture was heated for 2 h, cooled to room temperature, and the solution decanted from the residual solids. The solids were washed with EtOAc and the combined organic layers were washed with cold 15% H2SO4, saturated aqueous NaHCO3, and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents undr reduced pressure and column chromatography (10% EtOAc-hexanes) afforded the title compound as a yellow oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:FC1=CC=C(C=C1)C#CC(C[C@@H]1CC[Si@H](CC1)CCCCC)O;m1_m2_m3:O.C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m2_m3:C1=CC=CC=C1, and Products are 0:FC1=CC=C(C=C1)C#C\C=C\[C@@H]1CC[Si@H](CC1)CCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-(4-fluorophenyl)-4-(trans-4-pentyl-4-silacyclohexyl)-1-butyne-3-ol 8.0 g (24 mmol), p-toluenesulfonic acid monohydrate 1.6 g, and benzene 200 ml was heated under reflux to remove the water and then subjected to a conventional post-treatment. The reaction mixture thus obtained was not only a mixture of trans- and cis-isomers, with respect to the silacyclohexane ring, but also a mixture of E- and Z-isomers, with respect to the double bond. Hence, the product was separated by chromatography to give 1.2 g of the desired product of the trans-E isomer (yield 15.9%). |
Here is a chemical reaction formula: Reactants are:m3_m4:C1=CC=C2C(=C1)C(=C3C=CC=CC3=C2O)O;m3_m4:O=O;m2:C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O, Reagents are:, and Products are 0:OO;0:C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In all previously known anthraquinone processes, the oxidation reaction and the extraction take place in separate steps, and thus also in separate vessels. The oxidation reaction, in which anthrahydroquinone derivatives react with oxygen, forming hydrogen peroxide and anthraquinone derivatives, takes place in the oxidation reactor. From this reactor the organic working solution, which contains dissolved hydrogen peroxide, is directed to another vessel, wherein the hydrogen peroxide is removed by extracting it with water. In the oxidation reactor there are two phases, an organic working solution and an oxygen-containing gas phase. In the extraction vessel there are two liquid phases, an organic solution and an aqueous phase. Two phenomena essential for the process occur in the oxidation reactor, namely the dissolving of oxygen in the organic working solution and the oxidation reaction in the working solution. The key phenomenon occurring in the extraction vessel is the passing of the hydrogen peroxide from the working solution to the aqueous phase. |
Here is a chemical reaction formula: Reactants are:m2:C(CN)N;m1:C(C(O)C)(=O)O, Reagents are:m3:O, and Products are 0:C(CNC(C(O)C)=O)NC(C(O)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Lactic acid (441 g; 4.90 moles) was placed in a reaction flask equipped with a distillation head. Under a nitrogen atmosphere, ethylene diamine (147 g; 2.45 moles) was slowly added with stirring to the reaction flask. During the course of the addition, the reaction mixture turned a deep orange and the temperature reached 140° C. The reaction mixture was then heated at 150° C. overnight with the water being removed by distillation. The reaction mixture was allowed to cool to 125° C. then it was poured into an aluminum pan and allowed to cool to ambient temperature. to provide 468 g of crude product. This material was recrystallized from methanol (1.9 L) to provide N,N'-1,2-ethanediylbislactamide, m.p. 188° C. |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1:OC=1C=C2C=CC(=CC2=CC1)C(=O)O, Reagents are:m3:[Pd];m4:O1CCCC1, and Products are 0:OC1CC=2C=CC(=CC2CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: For example, 6-hydroxynaphthalene-2-carboxylic acid in a solvent such as tetrahydrofuran is reduced with hydrogen gas in the presence of a reducing catalyst such as a palladium/carbon under elevated pressure to obtain 5,6,7,8-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (1). |
Here is a chemical reaction formula: Reactants are:m1:OC=1C=C2CCC(CC2=CC1)C(=O)O;m2_m3:C(C1=CC=CC=C1)Br;m2_m3:[OH-].[K+], Reagents are:, and Products are 0:C(C1=CC=CC=C1)OC=1C=C2CCC(CC2=CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid obtained in the above manner is reacted with benzyl bromide in the presence of potassium hydroxide to obtain 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid (11). |
Here is a chemical reaction formula: Reactants are:m3:C(C)OCCOCC;m1:C1=C(C=CC2=CC=CC=C12)C(=O)O;m2:[Na], Reagents are:, and Products are 0:C1C(CCC2=CC=CC=C12)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The thus obtained 6-[4'-alkoxy-4-biphenyl)ethyl]-2-naphthalenecarboxylic acid (22) is hydrogenated in the presence of metal sodium in a solvent such as 1,2-diethoxyethane to obtain 6-[4'-alkoxy-4-biphenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (23). Finally, the resulting 6-[4'-alkoxy-4-biphenyl)ethyl]-1,2,3,4-tetrahydro-2-naphthalenecarboxylic acid (23) is reacted with an alcohol (24) having an asymmetric carbon in the presence of 4-N,N-dimethylaminoprydine, whereby the above-mentioned carboxylate compound (25) represented by the formula (II), in which x is --CH2CH2 --, may be obtained. |
Here is a chemical reaction formula: Reactants are:m5:Cl;m4:[OH-].[K+];m1_m2_m3_m7_m9_m8:OC=1C=C2CCC(CC2=CC1)C(=O)O;m1_m2_m3_m7_m9_m8:C(C1=CC=CC=C1)Br;m1_m2_m3_m7_m9_m8:[OH-].[K+], Reagents are:m1_m2_m3_m7_m9_m8:[I-].[Na+];m1_m2_m3_m7_m9_m8:O;m1_m2_m3_m7_m9_m8:C(C)O;m6:O, and Products are 0:C(C1=CC=CC=C1)OC=1C=C2CCC(CC2=CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 10.60 g (50 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid, 12.85 g (75 mmol) of benzyl bromide, 6.6 g (100 mmol) of 85% potassium hydroxide, 0.525 g (3.5 mmol) of sodium iodide, 200 ml of ethanol and 25 ml of distilled water was heated under reflux at 100° C. for 12 hours. To this reaction mixture was added 50 ml of 10% potassium hydroxide, followed by heating under reflux at that temperature for 2 hours. After allowing the reaction system to cool up to room temperature, the reaction mixture in cold water was acidified with 36% hydrochloric acid. The resulting deposited product was filtered, and recrystallized from toluene to obtain 13.08 g (46.4 mmol) of 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:[H][H];m1_m2_m3_m4:C(C1=CC=CC=C1)OC(=O)C1=CC=2CCC(CC2C=C1)OC(C1=CC=C(C=C1)OCCCCCCCCCC)=O, Reagents are:m1_m2_m3_m4:[Pd];m1_m2_m3_m4:O1CCCC1, and Products are 0:C(CCCCCCCCC)OC1=CC=C(C(=O)OC2CC=3C=CC(=CC3CC2)C(=O)O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Hydrogen gas was blown into a mixture of 0.53 g (1.0 mmol) of 6-(4'-decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid benzyl ester, 0.11 g of 5% palladium/carbon and 10 ml of tetrahydrofuran with stirring at room temperature and ordinary pressure for 15 hours. The reaction mixture was filtered using Celite as a filter aid, and the filtrate was concentrated to obtain 0.42 g (0.93 mmol) of 6-(4'-decyloxybenzoyloxy)-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m1:C(CCCCCCCCC)OC=1C=C2C=CC(=CC2=CC1)C(=O)O;m3_m2:Br, Reagents are:m3_m2:C(C)(=O)O, and Products are 0:OC=1C=C2CCC(CC2=CC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.6 g (50 mmol) of the 6-decyloxynaphthalene-2-carboxylic acid obtained in the first stage was heated under reflux at 130° C. for 7 hours in the presence of 250 cc of acetic acid and 86.5 g (0.5 mol) of 47% hydrobromic acid. To the reaction mixture was added distilled water, and then the resulting mixture was concentrated under reduced pressure to obtain 10.60 g (50 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m5:[OH-].[K+];m6:Cl;m1_m2_m3_m4_m9_m8:OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O;m1_m2_m3_m4_m9_m8:C(CCCCCCCCC)Br;m1_m2_m3_m4_m9_m8:[OH-].[K+];m1_m2_m3_m4_m9_m8:[I-].[Na+], Reagents are:m7:O;m1_m2_m3_m4_m9_m8:O;m1_m2_m3_m4_m9_m8:C(C)O, and Products are 0:C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 21.4 g (0.1 mol) of 4'-hydroxybiphenyl-4-carboxylic acid, 33.15 g (0.15 mol) of n-decyl bromide, 13.20 g (0.2 mol) of 85% potassium hydroxide, 1.05 g (7 mmol) of sodium iodide, 500 ml of ethanol and 100 ml of distilled water was heated under reflux at 100° C. for 12 hours. After 40 ml of 25% potassium hydroxide was added, the mixture was further heated under reflux for 2 hours. After allowing the reaction system to cool up to room temperature, the reaction mixture in cold water was acidified with 36% hydrochloric acid. The deposited product was separated by filtration and dissolved in acetone with heating, followed by filtration. The resulting filtrate was concentrated to obtain 1.97 g (6 mmol) of 4'-decyloxybiphenyl-4-carboxylic acid. |
Here is a chemical reaction formula: Reactants are:m1_m2:[H][H];m1_m2:FC([C@@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)OCC1=CC=CC=C1)(F)F, Reagents are:m3:[Pd];m4:O1CCCC1, and Products are 0:FC([C@@H](CCCCCC)OC(=O)C1CC2=CC=C(C=C2CC1)O)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Hydrogen gas was blown into a mixture of 8.19 g (18.3 mmol) of the 1,2,3,4-tetrahydro-6-benzyloxynaphthalene-2-carboxylic acid (R)-1-trifluoromethylheptyl ester obtained in the fourth stage, 3.6 g of 5% palladium/carbon as a catalyst and 50 ml of tetrahydrofuran with stirring at room temperature and ordinary pressure for 24 hours. The reaction mixture was filtered using Celite as a filter aid, and the filtrate obtained was concentrated to obtain 6.78 g (18.3 mmol) of 1,2,3,4-tetrahydro-6-hydroxynaphthalene-2-carboxylic acid (R)-1-trifluoromethylheptyl ester as a brown liquid. |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[H-].[H-].[H-].[Li+].[Al+3];m2:C(CCCCCCCCC)OC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)O, Reagents are:m1_m4:C(C)OCC;m3:C(C)OCC, and Products are 0:OCC1=CC=C(C=C1)C1=CC=C(C=C1)OCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.81 g (21.34 mmol) of LiAlH4 was introduced into 40 ml of diethyl ether and stirred. To the mixture was dropwise added a solution, prepared by introducing 1.71 g (5.06 mmol) of 4'-decyloxy-4-biphenylcarboxylic acid obtained in the first stage of Example 11 into 30 ml of diethyl ether, at room temperature over a period of 2 to 3 minutes, which was then continuously stirred for 5 days. After confirming the consumption of the raw material by TLC, to the resultant mixture was added 40 ml of water, and further added concentrated hydrochloric acid until the aqueous phase was approximately homogenized. The resultant solution was extracted with diethyl ether and dried, to obtain 4-hydroxymethyl-4'-decyloxybiphenyl. |
Here is a chemical reaction formula: Reactants are:m1:[OH-].[Na+];m8:ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O;m3_m4:O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO;m3_m4:ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O;m2:S(O)(O)(=O)=O;m7:O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO;m6:O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO;m5:ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O, Reagents are:, and Products are 0:ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A culture was obtained by the same method as in Example 1 using Geotrichum eriense ATCC 22311 as the microorganism and then adjusted to pH 6 with an aqueous sodium hydroxide solution and an aqueous sulfuric acid solution. A 25-ml portion of this culture, 1 g of glucose and (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanone were mixed up in a 500-ml Sakaguchi flask and the mixture was shaken for 1 day to thereby allow the reaction to proceed. Then, again, 250 mg of (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanone was added. The reaction was allowed to proceed for further 2 days with shaking while the glucose concentration was controlled within the range of 0 to 4% by adding glucose portionwise. Thereafter, a further 250 mg portion of (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanone was added and shaking was continued for further 4 days to allow the reaction to proceed while controlling the glucose concentration in the same manner as mentioned above. The reaction mixture was diluted with 100 ml of water and extracted with 100 ml portion of ethyl acetate for 3 times. The organic extract layers were combined, washed with 100 ml of water and further with 100 ml of a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. This solution was concentrated to dryness to give (2S,3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanol as a white solid (607 mg; yield 67%; purity 83.7 wt %; selectivity 2S,3S/2R,3S=97/3; optical purity 99.7% ee). |
Here is a chemical reaction formula: Reactants are:m3:ClCC([C@H](CC1=CC=CC=C1)NC(=O)OC)=O;m1:[OH-].[Na+];m2:S(O)(O)(=O)=O, Reagents are:, and Products are 0:ClC[C@H]([C@H](CC1=CC=CC=C1)NC(=O)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A culture was obtained by the same method as in Example 1 using Candida gropengiesseri IFO 0659 as the microorganism and adjusted to pH 6 with an aqueous sodium hydroxide solution and an aqueous sulfuric acid solution. A 75-ml portion of this culture was separated into a supernatant and cells by centrifugation. To the whole amount of the cells was added a portion of the supernatant to make the total volume 25 ml. This cell suspension (25 ml), 1 g of glucose and 250 mg of (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanone were mixed together in a 500-ml Sakaguchi flask and the mixture was shaken for 1 day to allow the reaction to proceed. A further 250-mg portion of (3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanone was added. The reaction was allowed to proceed by shaking for further 6 days while controlling the glucose concentration within the range of 0 to 4% by adding glucose portionwise. Water, 100 ml, was added to the reaction mixture and the whole mixture was extracted with 100 ml portion of ethyl acetate for 3 times. The organic extract layers were combined, washed with 100 ml of water and further with 100 ml of a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. This solution was concentrated to dryness to give (2S,3S)-1-chloro-3-methoxycarbonylamino-4-phenyl-2-butanol as a white solid (401 mg; yield 61%; purity 76.8 wt %; selectivity 2S,3S/2R,3S=98/2; optical purity 98.3% ee). |
Here is a chemical reaction formula: Reactants are:m3_m0:C(C)O;m1:O=C[C@H](O)[C@@H](O)[C@H](O)CO;m2:O=C[C@H](O)[C@@H](O)[C@H](O)CO;m4:C(C)O, Reagents are:, and Products are 0:O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The results presented in FIG. 2 show that in contrast to the control strain containing the shuttle vector alone (CP4[pZB 186]), the recombinant containing the added xylose isomerase, xylulokinase, transaldolase and transketolase genes demonstrated growth and ethanol production from xylose as a carbon source. The recombinant strain produces ethanol from glucose as efficiently as the control strain at 94% of theoretical yield. The recombinant strain additionally produces ethanol from xylose at 84% of theoretical yield in 79 hours. Furthermore, in the combined presence of glucose and xylose, the recombinant strain ferments both sugars simultaneously to ethanol at 88% of theoretical yield within 48 hours, thus providing the foundation for advanced process designs with cofermentation of mixed-sugar feedstocks. |
Here is a chemical reaction formula: Reactants are:m3:FCC(=O)OCC;m4:[Cl-].[NH4+];m1_m5:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1Br;m2:C(CCC)[Li], Reagents are:m1_m5:O1CCCC1;m6:C(C)OC(C)=O, and Products are 0:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CF)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.98 g (0.0mole) of N-t-butyl-3-bromo-2-thiophenesulfonamide was dissolved in 50mi of dry tetrahydrofuran and the mixture was cooled to -78° C. under nitrogen gas. To the reaction solution was slowly added dropwise 8.4 ml of n-butyl lithium (2.5N) and then the temperature of the mixture was raised slowly to -20° C. and again cooled to -78° C. 1.2 g (0.011 mole) of ethyl fluoroacetate was added slowly to the reaction mixture. The temperature of the mixture was raised again slowly to -20° C. and then the mixture was stirred for 10 minutes. To the reaction mixture was added 100 ml of 5% aqueous ammonium chloride solution, and then added 100 ml of ethylacetate to separate the organic layer. The extracted organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjeced to column chromatography on silica gel to obtain 2.0 g (Yield: 72%) of the pure title compound as a liquid. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CF)OC(C)=O, Reagents are:m1_m2:FC(C(=O)O)(F)F, and Products are 0:C(C)(=O)OC(CF)C1=C(SC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.4 g (0.0043 mole) of N-t-butyl-3-(1-aceoxy-2-fluoroethyl) -2-thiophenesulfonamide synthesized in Example 2 dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride and washed with aqueous sodium bicarbonate solution. The organic layer was separated, dried over anhydrous magnesium sulfate and then filtered. The filtrate was concentrated. The residue was recrystallized to obtain 750 mg (Yield: 74%) of the pure title compound as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1_m3:COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)OC(C)=O, Reagents are:m1_m3:[OH-].[Na+], and Products are 0:COC1=NC(=NC(=C1)OC)NC(=O)NS(=O)(=O)C=1SC=CC1C(CF)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 650 mg (0.0015 mole) of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-3-(1-acetoxy-2-fluoroethyl)-2-thiophenesulfonamide synthesized in Example 4 was dissolved in 5 ml of aqueous sodium hydroxide solution and then stirred at normal temperature for one hour. The reaction mixture was adjusted to pH4 by adding 5% aqueous HCl solution and then extracted with methylene chloride. The extract was concentrated to obtain 540 mg (Yield: 92%) of the pure title compound. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)=O;m1_m3_m4:C(C)(=O)O;m2:C(#N)[BH3-].[Na+], Reagents are:m1_m3_m4:O1CCCC1, and Products are 0:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)OC(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.5 g (0.005 mole) of N-t-butyl-3-(chloroacetyl)-2-thiophenesulfonamide synthesized in Example 6 was dissolved in the combined solution of 1 ml of acetic acid and 10 ml of tetrahydrofuran and then 0.31 g (0.005 mole) of sodium cyanoborohydride was added slowly thereto. The reaction solution was stirred at normal temperature for 30 minutes and then subjected to a vacuum evaporator to remove the solvent. To the residue was added 10 ml of water and then the resulting solution was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and filtered. To the filtrate were added acetic anhydride, pyridine and N,N-dimethylaminopyridine and the mixture was stirred at normal temperature for 24 hours and then washed with 5% aqueous hydrochloric acid solution. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated and the residue was subjected to column chromatography on silica gel to obtain 5 g (Yield: 84%) of the title compound. 1H NMR(CDCl3, δ): 1.3(s, 9H), 2.15(s, 3H), 3.57-3.9(m, 2H), 5.23(s, 1H), 6.5(m, 1H), 7.13(d, 1H), 7.5 (d, 1H) |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(C)(C)NS(=O)(=O)C=1SC=CC1C(CCl)OC(C)=O, Reagents are:m1_m2:FC(C(=O)O)(F)F, and Products are 0:C(C)(=O)OC(CCl)C1=C(SC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.5 g (0.0044 mole) of N-t-butyl-3-(1-acetoxy-2-chloroethyl)-2-thiophenesulfonamide synthesized in Example 7 was dissolved in 5 ml of trifluoroacetic acid. The reaction solution was stirred at normal temperature for 12 hours and then concentrated under reduced pressure. The residue was dissolved in methylene chloride and the solution was washed with aqueous sodium bicarbanate solution. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was then concentrated. The residue was subjected to column chromatograpy on silica gel to obtain 760 mg (Yield: 72%) of the pure title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3_m5:O.Cl.C(C1=CC=CC=C1)(=N)N;m1_m2_m4_m3_m5:C[O-].[Na+];m1_m2_m4_m3_m5:C(C)C(C(=O)OCC)C(=O)OCC, Reagents are:m1_m2_m4_m3_m5:CO;m1_m2_m4_m3_m5:CO, and Products are 0:C(C)C=1C(NC(=NC1O)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 mL of water and the pH was adjusted to 7 with concentrated hydrochloric acid. The solid precipitate was collected by filtration and dried under vacuum at 50° C. to afford 31.89 g (51%) of crude 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone as a pale yellow solid. 1H-NMR (d6-DMSO) δ 1.05(3H,t), 2.39(2H,q), 7.5(3H,m), 8.1(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:O.Cl.C(C1=CC=CC=C1)(=N)N;m1_m2_m3_m4:C(C)(=O)[O-].[Na+];m1_m2_m3_m4:C(C)OC(=CC(=O)OCC)OCC;m1_m2_m3_m4:CS(=O)C, Reagents are:m5:[OH-].[Na+], and Products are 0:C(C)OC1=CC(NC(=N1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3.14 g (20.0 mmol) of benzamidine hydrochloride hydrate, 1.65 g (20.1 mmol) of powdered anhydrous sodium acetate, 4.17 g (22.2 mmol) of ethyl 3,3-diethoxyacrylate and 10 mL of DMSO was heated at 120° C. for 8 h. The mixture was cooled, diluted with 50 mL of 5% aqueous NaOH and washed with two 100 mL portions of ether. The aqueous layer was acidified with concentrated hydrochloric acid and the precipitate was collected by filtration and dried under vacuum at 50° C. to furnish 2.28 g (57%) of crude 6-ethoxy-2-phenyl-4(3H)-pyrimidinone as a yellow solid 1 H-NMR (d6-DMSO) δ 1.35(3H,t), 4.33(2H,q), 5.60(1H,s), 7.50(3H,m), 8.2(2H,m). |
Here is a chemical reaction formula: Reactants are:m2:BrN1C(CCC1=O)=O;m1_m3:C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C(F)(F)F, Reagents are:m1_m3:CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C, and Products are 0:BrC=1C(NC(=NC1C(F)(F)F)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.0 g (3.94 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone and 20 mL of glacial acetic add was added 1.0 g (5.6 mmol) N-bromosuccinimide and the mixture was left to stir at room temperature for 16 h. The reaction was poured onto ice water and vacuum filtered, washing well with water. The crude product was recrystallized from ethyl acetate to yield 1.05 g (83.5%) of 5-bromo-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, as a white solid. 1H-NMR (d6DMSO) δ 7.6(3H,m); 8.15(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m3:C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C1=CC=CC=C1;m2:BrN1C(CCC1=O)=O, Reagents are:m1_m3:C(C)(=O)O, and Products are 0:BrC=1C(NC(=NC1C1=CC=CC=C1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 13.37 g (56 mmol) of 2,6-diphenyl-4(3H)-pyrimidinone and 200 mL glacial acetic acid was added 15.1 g (84.8 mmol) of N-bromosuccinimide and the mixture was left to stir at room temperature for 60 h. The reaction was poured onto 100 g crushed ice and vacuum filtered, washing well with water, then air dried to yield 8.85 g (48%) 5-bromo-2,6-diphenyl-4(3H)-pyrimidinone, as a white solid. 1H-NMR (d6DMSO) δ 7.55(6H,m); 7.75(2H,m); 8.15(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)C1=CC(NC(=N1)C1=CC=CC=C1)=O;m1_m2_m3_m4:[OH-].[Na+];m1_m2_m3_m4:II, Reagents are:m1_m2_m3_m4:O, and Products are 0:C(C)C1=C(C(NC(=N1)C1=CC=CC=C1)=O)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 8.18 g (40.9 mmol) of 6-ethyl-2-phenyl-4(3H)-pyrimidinone, 1.68 g (42.0 mmol) of sodium hydroxide, 10.42 g (41.0 mmol) of iodine and 50 mL of water was heated at 50° C. for 4 h. The mixture was cooled and filtered. The white solid collected was dried in a vacuum oven to leave 12.60 g (75%) of 6-ethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone. 1 H-NMR (d6-DMSO) δ 1.25(3H,t), 2.85(2H,q), 7.50(3H,m), 8.15(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:IC=1C(NC(=NC1OC1=CC=CC=C1)C1=CC=CC=C1)=O, Reagents are:m4:[Zn];m1_m2_m5:[Zn];m1_m2_m5:C(C)(=O)O;m3:[Zn], and Products are 0:O(C1=CC=CC=C1)C1=CC(NC(=N1)C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 7.07 g (18.1 mmol) of crude 5-iodo-6-phenoxy-2-phenyl-4(3H)-pyrimidinone, 2.02 g (31.1 mmol) of zinc dust and 25 mL of glacial acetic acid was heated to reflux. After 15 min an additional 2.06 g (31.7 mmol) of zinc dust was added, followed 15 min later by a further 2.04 g (31.4 mmol) of zinc dust. The mixture was maintained at reflux for 2 h, cooled and filtered to remove unreacted zinc. The filtrate was rotovaped to leave a semi-solid which was triturated with 75 mL of boiling water to afford 6.01 g (57% from 4,6-dihydroxy-2-phenylpyrimidine) of 6-phenoxy-2-phenyl-4(3H)-pyrimidinone as a yellow solid. 1H-NMR (d6-DMSO) δ 5.5(1H,s), 7.1-7.5(8H), 8.1(2H). |
Here is a chemical reaction formula: Reactants are:m1_m3_m4_m2:C(C)OC(=O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C;m1_m3_m4_m2:[OH-].[Na+], Reagents are:m1_m3_m4_m2:C(C)O;m1_m3_m4_m2:C1CCOC1, and Products are 0:C(=O)(O)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.81 g (6.1 mmol) of 6-ethoxycarbonyl-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone in 100 mL of ethanol and 50 mL of THF was added 50 mL of 5% aqueous sodium hydroxide. The mixture was stirred at room temperature for 24 h and rotovapped to remove the bulk of the organic solvents. The residue was diluted with 50 mL of 5% aqueous sodium hydroxide and washed with 100 mL of ether. The aqueous phase was acidified with concentrated hydrochloric acid and extracted with two 100 mL portions of ethyl acetate. The combined ethyl acetate extracts were washed with 50 mL of brine, dried over MgSO4 and concentrated to leave 0.87 g (53%) of crude 6-carboxy-5-methyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone as a brown oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O;m1_m2_m4_m3:C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O;m1_m2_m4_m3:[OH-].[Na+], Reagents are:m5:C(C)(=O)OCC;m1_m2_m4_m3:C1CCOC1, and Products are 0:C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC(C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 4.83 g (15.8 mmol) of 5-ethyl-3-propargyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 46) in 50 mL of THF was added 50 mL of 10% aq NaOH. The mixture was heated at reflux for 2 h, cooled and diluted with 150 mL of ethyl acetate. The organic layer was separated, washed with 50 mL of water and 50 mL of brine and dried over MgSO4. Removal of the solvent afforded 4.74 g of 5-ethyl-3-(2-oxopropyl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 179) as a white solid. 1H-NMR (CDCl3) 1.2(3H), 2.2(3H,s), 2.7(2H,q), 4.7(2H,s), 7.45(5H,m). |
Here is a chemical reaction formula: Reactants are:m5_m7:[OH-].[Na+];m4:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3;m1_m2_m9_m3:C1(=CC=CC=C1)C1=NC(=CC(N1)=O)C(F)(F)F;m1_m2_m9_m3:COCOC;m1_m2_m9_m3:O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3, Reagents are:m5_m7:C(Cl)Cl;m8_m6:CCCCCC;m8_m6:C(C)(=O)OCC;m1_m2_m9_m3:C(Cl)(Cl)Cl, and Products are 0:COCN1C(=NC(=CC1=O)C(F)(F)F)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.5 g (5.9 mmol) of 2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone, 17.2 g (226.3 mmol) dimethoxymethane, and 35 mL of chloroform was added 2.5 g (17.6 mmol) phosphorous pentoxide, at room temperature. By TLC (25% ethyl acetate in hexane) the reaction was incomplete after 4 h and an additional 3 g (21.1 mmol) phosphorous pentoxide was added. Stirring was continued for 16 h. The reaction mixture was poured onto crushed ice and 1M sodium hydroxide and methylene chloride were added. The layers were separated and the aqueous layer was extracted twice with methylene chloride. The organic extracts were combined and washed with brine, then dried over MgSO4 and concentrated to yield 1.1 g crude product, which was purified by recrystallization from hexane. Thus, 0.55 g (32%) 3-methoxymethyl-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (Compound 6) as a yellow solid was obtained. 1H-NMR (CDCl3) δ 3.55(3H,s); 5.2(2H,d); 6.85(1H,s); 7.65(3H,m); 7.75(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#C)=O;m1_m2_m3:C(=C)I, Reagents are:m1_m2_m3:C(C)N(CC)CC;m4_m5:[Cu]I;m4_m5:[Pd](Cl)Cl.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, and Products are 0:C(C)C=1C(N(C(=NC1C(F)(F)F)C1=CC=CC=C1)CC#CC=C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a deoxygenated solution of 1.01 g (3.28 mmol) of 5-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-4(3H)-pyrimidinone and 0.61 g (3.96 mmol) of vinyl iodide in 25 mL of triethylamine was added a mixture of 60 mg of copper (I) iodide and 60 mg of bis(triphenylphosphine) palladium (II) chloride. The mixture was stirred at room temperature for 22 h and rotovapped to remove the bulk of the triethylamine. The residue was taken up in 150 mL of ethyl acetate, washed with 75 mL of 5% aqueous hydrochloric acid, 75 mL of saturated aqueous sodium bicarbonate and 75 mL of brine, and dried. Removal of the solvent left 1.51 g of a brown tar. Flash chromatography on a column of 30 g of silica gel eluting with 20, 40, 60 and 60% ether in hexanes afforded 0.31 g of crude 5-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone. A second chromatography yielded 0.25 g (23%) of pure 5-ethyl-3-(pent-2-yn-4-en-1-yl)-2-phenyl-6-trifluoromethyl-4(3H)-pyrimidinone (compound 111) as a solid, mp 104°-106° C. 1H-NMR (CDCl3) d 1.25(3H,t), 2.8(2H,q), 4.75(2H,s), 5.5-5.9(3H,m), 7.55(3H,m), 7.7(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C1OCCO1)CC#C)=O;m1_m5_m2:Cl;m3_m4:CCOCC;m3_m4:O, Reagents are:m1_m5_m2:C(C)(=O)OCC;m7:C(C)(=O)OCC;m6:CCCCCC, and Products are 0:C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2.3 g (6.8 mmol) of 5,6-diethyl-2-[3-(2-dioxolanyl)phenyl]-3-propargyl-4(3H)-pyrimidinone in 1 mL of ethyl acetate was added 50 mL of 6M hydrochloric acid and the mixture was stirred for 4 hours. The reaction was followed by gas chromatography and TLC(20% ethyl acetate in hexane). Upon completion of reaction, 75 mL of ether and 150 mL of water were added to the reaction mixture. The layers were separated and the aqueous layer was extracted twice with 50 mL of ether. The organic layers were combined, dried over MgSO4 and concentrated to yield 1.73 g of 5,6-diethyl-2-(3-formylphenyl)-3-propargyl-4(3H)-pyrimidinone (Compound 69) as a yellow oil (86%), which solidified on standing. Mp.=82°-86° C. 1H-NMR (CDCl3) δ 1.25(6H,m), 2.4(1H,t), 2.65(4H,q), 4.6(2H,d), 7.7(1H,t), 8.05(2H,m), 8.25(1H,s), 10.15(1H,s). |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3:C(C)N1C(=NC(=C(C1=O)I)CC)C1=CC=CC=C1;m1_m5_m2_m3:FC(C(=O)[O-])(F)F.[Na+];m1_m5_m2_m3:CN1C(CCC1)=O, Reagents are:m4:CCOCC;m1_m5_m2_m3:[Cu]I, and Products are 0:C(C)N1C(=NC(=C(C1=O)C(F)(F)F)CC)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.00 g (2.8 mmol) of 3,6-diethyl-5-iodo-2-phenyl-4(3H)-pyrimidinone, 1.08 g (5.7 mmol) of copper (I) iodide, 1.54 g (11.3 mmol) of sodium trifluoroacetate and 8 mL of anhydrous N-methylpyrrolidinone was heated at 175 C for 2 h. The mixture was cooled, diluted with 175 mL of ether, washed with four 50 mL portions of water and dried over MgSO4. Removal of the solvent on the rotovap afforded 0.92 g of crude product as a brown oil. This material was purified by flash chromatography on a 25 g column of silica gel eluting with 100 mL portions of 0, 10, 20, 30, 40, 50 and 75% ether in hexanes to afford 0.35 g of 3,6-diethyl-2-phenyl-5-trifluoromethyl-4(3H)-pyrimidinone (compound 185) as a white solid. 1H-NMR (CDCl3) 1.25(3H,t), 1.30(3H,t), 2.8(2H,q), 4.0(2H,q), 7.5(5H). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)C=1C(N(C(=NC1CC)C1=CC(=CC=C1)C=O)CC#C)=O;m1_m2_m3:Cl.NO, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C(C)C=1C(N(C(=NC1CC)C=1CC(C=CC1)=NO)CC#C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 100 mL RBF were charged 1.1 g (3.7 mmol) of 5,6-diethyl-2-(3-formyl-phenyl)-3-propargyl-4(3H)-pyrimidinone, 0.52 g (7.5 mmol) of hydroxylamine hydrochloride and 50 mL of ethanol. The reaction mixture was refluxed for 17 hours. The ethanol was removed in vacuo and ether and ethyl acetate were added to the residue. The organics were washed 3 times with water. The organic layer was gravity filtered to remove 0.22 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139). The organic layer was dried over MgSO4 and concentrated to yield a further 0.67 g of 5,6-diethyl-2-(3-hydroxyiminophenyl)-3-propargyl-4(3H)-pyrimidinone (compound 139) as a white solid. A combined yield of 77.6% was obtained. 1H-NMR (CDCl3) 1.25(6H,m); 2.35(1H,t); 2.65(4H,m); 4.6(2H,d); 7.49-8.15(4H,m); 8.7(1H,s) |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC;m1_m2_m4_m3:C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)CC(=O)OC;m1_m2_m4_m3:[NH4+].[OH-], Reagents are:m1_m2_m4_m3:C1CCOC1, and Products are 0:NC(=O)CC=1C(N(C(=NC1CC)C1=CC=CC=C1)CC#C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred solution of 1.75 g (5.7 mmol) of 6-ethyl-5-methoxycarbonylmethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 105) in 100 mL of THF was added 200 mL of concentrated aqueous NH4OH. The mixture was stirred for 2 weeks and the bulk of the THF was removed on the rotovap. The mixture was shaken with 100 mL of ethyl acetate and filtered. The solid collected was dried in a vacuum oven at 50° C. to afford 0.57 g of 5-aminocarbonylmethyl-6-ethyl-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 275), m.p. 196°-198° C. 1H-NMR (d6 -DMSO) 1.15(3H,t), 2.5(2H,q), 3.2(1H,t), 3.4(2H,s), 4.55(2H,d), 6.9(1H,br s), 7.35(1H,br s), 7.55(3H,m), 7.7(2H,m). The aqueous layer of the filtrate was extracted with two additional 100 mL portions of ethyl acetate. The combined ethyl acetate extracts were dried over MgSO4 and rotovaped to afford a further 0.54 g of Compound 275. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)OC;m1_m2:C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)OC, Reagents are:m3:O, and Products are 0:C(C)C1=C(C(N(C(=N1)C1=CC=CC=C1)CC#C)=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To an oven dried 3-neck round bottom flask, equipped with a magnetic stirrer, a thermometer, an addition funnel, a septum and a nitrogen inlet, was added 10 mL of 1M boron tribromide in methylene chloride, by syringe. The BBr3 was cooled to -65 C with a dry ice/acetone bath and 0.9 g (3.3 mmol) of 6-ethyl-5-methoxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone (Compound 183) was added dropwise through an addition funnel. The reaction stirred at low temperature for 1.5 h. The reaction progress was checked by G.C. and was complete at this time. Water was slowly added and the reaction was left to stir for 1 h at room temperature. The reaction mixture was transferred to an addition funnel and extracted three times with methylene chloride. The organic layers were combined and dried over MgSO4, then concentrated to yield 0.6 g (72% yield) of 6-ethyl-5-hydroxy-2-phenyl-3-propargyl-4(3H)-pyrimidinone, as a white solid. M.p. 152°-154° C. 1H-NMR (CDCl3) 1.25(3H,t), 2.4(1H,t), 2.7(2H,q), 4.65(2H,d), 6.25(1H,s), 7.55(3H,m), 7.65(2H,m). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CN=C=O;m1_m2_m3:FC1=C(N)C=CC(=C1)F, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:FC1=C(C=CC(=C1)F)NC(=O)NC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Methyl isocyanate (9.6 g, 10 mL, 0.174 mol) is added to a solution of 2,4-difluoroaniline (15 g, 0.116 mol) in toluene. The reaction mixture is stirred for 1 hour and filtered to obtain a solid. The solid is washed with hexanes and air-dried to give the title product as an off-white solid, mp 182°-183° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:[N+](=O)(O)[O-];m1_m2_m3:ClC1=C(C=CC(=C1)F)N1C(N(C(NC1=O)=O)C)=O, Reagents are:m1_m2_m3:S(O)(O)(=O)=O, and Products are 0:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(NC1=O)=O)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Nitric acid (70% real, 8.3 mL, 0.131 mol) is added to a solution of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (32.4 g, 0.119 mol) in concentrated sulfuric acid while maintaining the reaction mixture temperature below 10° C. After the addition is complete, the reaction mixture is stirred at room temperature for 30 minutes, cooled to 10° C and diluted with ice-water. The resultant aqueous mixture is filtered to obtain a solid which is washed with water and air-dried to give the title product as a white solid (28.5 g, mp 135°-139° C.). |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1_m3_m4:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(NC1=O)=O)C)=O, Reagents are:m1_m3_m4:[Pt];m1_m3_m4:C(C)(=O)OCC, and Products are 0:NC=1C(=CC(=C(C1)N1CN(CN=C1)C)Cl)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-(2-chloro-4-fluoro-5-nitrophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (28.5 g, 0.09 mol) and 5% platinum on activated carbon (1 g) in ethyl acetate is hydrogenated at 55 psi until hydrogen uptake is complete. The reaction mixture is then filtered and concentrated in vacuo to give the title product as a white solid, mp 244°-245° C. |
Here is a chemical reaction formula: Reactants are:m1_m5:FC1=C(C=C(C=C1)N=C=O)[N+](=O)[O-];m3:C(C)N(CC)CC;m4:O;m2:Cl.C(C)OC(CN)=O, Reagents are:m1_m5:O1CCCC1, and Products are 0:FC1=C(C=C(C=C1)NC(=O)NCC(=O)OCC)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 4-fluoro-3-nitrophenyl isocyanate (10 g, 0.055 mol) in anhydrous tetrahydrofuran is cooled to 0° C., treated with glycine ethyl ester hydrochloride (7.7 g, 0.055 mol), treated with triethylamine (5.56 g, 0.055 mol) while maintaining the temperature below 10° C., stirred at room temperature for 1 hour and poured into water. The aqueous mixture is extracted with ether. The combined organic extracts are washed sequentially with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a solid which is air-dried to give the title product as a yellow solid (8.8 g, mp 115°-120° C.). |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1_m3_m4:FC1=C(C=C(C=C1)NC(=O)NCC(=O)OCC)[N+](=O)[O-], Reagents are:m1_m3_m4:[Pt];m1_m3_m4:C(C)(=O)OCC, and Products are 0:NC=1C=C(C=CC1F)NC(=O)NCC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of N-[(4-fluoro-3-nitrophenyl)carbamoyl]glycine, ethyl ester (8 g, 0.029 mol) and 5% platinum on activated carbon (0.5 g) in ethyl acetate is hydrogenated at 50 psi until hydrogen uptake is complete. The reaction mixture is then filtered and cooled in an ice-bath until a solid forms. The solid is collected by filtration and air-dried to give the title product as a white solid (4.5 g, mp 152°-153° C.). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:ClC1=C(C=CC(=C1)F)N1C(N(C(NC1=O)=O)C)=O;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m5:BrCC(=O)OC(C)C;m4:O, Reagents are:m6:C(Cl)Cl;m1_m2_m3_m5:CN(C=O)C;m7:CCOCC, and Products are 0:ClC1=C(C=CC(=C1)F)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-(2-chloro-4-fluorophenyl)-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (40.9 g, 0.150 mol), potassium carbonate (31.1 g, 0.225 mol) and isopropyl bromoacetate (29.1 mL, 0.225 mol) in N,N-dimethylformamide is stirred at room temperature for 2 hours, poured into water and extracted with ethyl acetate. The organic extract is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an oil. Flash column chromatography of the oil using silica gel and 0% to 10% ether in methylene chloride solutions gives the title product as a white solid (51.5 g, mp 127°-128° C.). |
Here is a chemical reaction formula: Reactants are:m5:[N+](=O)(O)[O-];m1_m6:ClC1=C(C=CC(=C1)F)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O;m2:[N+](=O)(O)[O-];m4:[N+](=O)(O)[O-];m3:[N+](=O)(O)[O-], Reagents are:m1_m6:S(O)(O)(=O)=O, and Products are 0:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of isopropyl 3-(2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (48.7 g, 0.0508 mol) in concentrated sulfuric acid is cooled to 0° C., treated with 90% nitric acid (2.6 mL), stirred at room temperature overnight, treated with 90% nitric acid (1.0 mL), stirred for 4 hours, treated with 90% nitric acid (2.0 mL), stirred at room temperature overnight, treated with 90% nitric acid (1.0 mL), stirred for 1 hour and poured onto ice. The resultant aqueous solution is filtered to obtain a solid. A solution of the solid in ether is dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a yellow foam which is identified by NMR spectral analyses. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)O)=O;m1_m2_m3:S(O)(O)(=O)=O;m1_m2_m3:CC(C)O, Reagents are:, and Products are 0:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3-(2-chloro-4-fluoro-5-nitrophenyl)-tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetic acid (43.6 g, 0.105 mol) and concentrated sulfuric acid (25 mL) in 2-propanol (300 mL) is refluxed for 12 hours, cooled to room temperature and filtered to obtain a solid. The solid is dried to give the title product as an off-white solid which is identified by NMR spectral analyses. The filtrate is partially concentrated in vacuo and poured over ice. The resultant aqueous mixture is extracted with ethyl acetate and the organic extract is dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain an orange oil. Flash column chromatography of the oil using silica gel and 2.5% to 5% ether in methylene chloride solutions gives additional title product as a yellow foam. |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m4:[H][H];m1_m5_m6:ClC1=C(C=C(C(=C1)F)[N+](=O)[O-])N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O;m3:CCOCC, Reagents are:m1_m5_m6:[Pt];m1_m5_m6:C(C)(=O)OCC;m8_m9:[Pt];m8_m9:C(C)(=O)OCC;m7:C(Cl)Cl, and Products are 0:NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of isopropyl 3-(2-chloro-4-fluoro-5-nitrophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (34.8 g, 0.0835 mol) and 5% platinum on carbon (3.48 g) in ethyl acetate is hydrogenated until about 90 psi of hydrogen is taken up. The reaction mixture is then filtered and concentrated in vacuo to obtain a foam. Column chromatography of the foam using silica gel and 10% to 20% ether in methylene chloride solutions gives a yellow foam which contains two compounds. A mixture of the foam and 5% platinum on carbon (3.5 g) in ethyl acetate is hydrogenated until 5 psi of hydrogen is taken up. The reaction mixture is then filtered and concentrated in vacuo to give the title product as a yellow foam which is identified by NMR spectral analyses. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3_m4:NCCS;m1_m2_m5_m3_m4:C(C)N(CC)CC;m1_m2_m5_m3_m4:BrC(C(=O)OCC)CBr;m1_m2_m5_m3_m4:C(Cl)(Cl)Cl.C1(=CC=CC=C1)C, Reagents are:m1_m2_m5_m3_m4:C(Cl)(Cl)Cl, and Products are 0:N1C(CSCC1)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A warm solution of 2-aminoethanethiol (10.0 g, 0.130 mol) and triethylamine (36 mL, 0.260 mol) in chloroform is added over 5 minutes to a solution of ethyl 2,3-di-bromopropionate (33.9 g, 0.130 mol) in a chloroform/toluene (1:1.6) solution. The reaction mixture is stirred at room temperature for 2.5 hours, filtered and concentrated in vacuo to obtain an orange liquid. The liquid is vacuum distilled to give the title product as a colorless liquid, bp 121°-124° C. at 3 mm Hg. |
Here is a chemical reaction formula: Reactants are:m3_m7_m9_m8_m0:CCOCC;m2_m5:I(=O)(=O)(=O)[O-].[Na+];m1_m4:ClC1=C(C=C(C(=C1)F)N1C(N2C(CSCC2)C1=O)=O)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O, Reagents are:m3_m7_m9_m8_m0:C(Cl)Cl;m3_m7_m9_m8_m0:C(Cl)Cl;m3_m7_m9_m8_m0:CO;m2_m5:O;m1_m4:CO;m6:C(Cl)Cl, and Products are 0:ClC1=C(C=C(C(=C1)F)N1C(N2C(CS(CC2)=O)C1=O)=O)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of isopropyl 3-{2-chloro-4-fluoro-5-[5,6,8,8a-tetrahydro-1,3-dioxo-1H-imidazo[5,1-c][1,4]-thiazin-2(3H)-yl]phenyl}tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (0.95 g, 1.75 mmol) in methanol (10 mL) is added over 15 minutes to a solution of sodium periodate (0.38 g, 1.78 mmol) in water (10 mL) which is previously cooled to 0°-5° C. After the addition is complete, the reaction mixture is stirred at room temperature overnight, diluted with methylene chloride, washed sequentially with a one molar KH2PO4 solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow foam. Flash column chromatography of the foam using silica gel, a 10% ether in methylene chloride solution and a 2.5% methanol in methylene chloride solution gives the title product as a white foam (0.59 g, mp 175°-180° C.). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrCCCCBr;m1_m2_m3_m4:C(=O)(OCC)NNC(=O)OCC;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m3_m4:C(C)#N, and Products are 0:N1(N(CCCC1)C(=O)OCC)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1,4-Dibromobutane (81.4 mL, 0.682 mol) is added over 1 hour to a mixture of 1,2-dicarbethoxyhydrazine (100 g, 0.568 mol) and potassium carbonate (158 g, 1.14 mol) in acetonitrile (600 mL). The resultant reaction mixture is refluxed for 6 hours, cooled to room temperature, and filtered. The filtrate is concentrated in vacuo to obtain a yellow liquid which is distilled under reduced pressure to give the title product as a colorless liquid (90.8 g, bp 115°-120° C. at 0.9 mm Hg). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(=S)(Cl)Cl;m1_m2_m3_m4:NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F;m1_m2_m3_m4:C(C)N(CC)CC, Reagents are:m5:O1CCCC1;m1_m2_m3_m4:O1CCCC1, and Products are 0:ClC1=C(C=C(C(=C1)F)N=C=S)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Thiophosgene (0.50 mL, 6.5 mmol) is added over 45 minutes to a solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (2.5 g, 6.5 mmol), and triethylamine (1.8 mL, 13.0 mmol) in tetrahydrofuran. The reaction mixture is stirred at room temperature for 4 hours, diluted with tetrahydrofuran, and filtered. The filtrate is concentrated in vacuo to give the title product as an orange oil which is identified by NMR spectral analyses, Using essentially the same procedure, but using the appropriately substituted 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-2,4,6-trioxo-s-triazine, the following compounds are obtained: |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)OCC;m1_m2_m3_m5:C(C)(=O)Cl;m1_m2_m3_m5:ClC1=CC(=C(N)C=C1)F;m1_m2_m3_m5:C(C)N(CC)CC, Reagents are:m6:C(C)O;m1_m2_m3_m5:O1CCCC1, and Products are 0:ClC1=CC(=C(NC(C)=O)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Acetyl chloride (24.2 mL, 0.34 mol) is added slowly to a solution of 4-chloro-2-fluoroaniline (49.4 g, 0.34 mol), and triethylamine (47 mL, 0.34 mol) in tetrahydrofuran while maintaining the reaction mixture temperature below 20° C. After the addition is complete, the reaction mixture is stirred overnight at room temperature, and poured into ethyl acetate. The organic solution is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an off-white solid. A mixture of the solid in ethanol is stirred for several minutes, and filtered to give the title product as a white solid. |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)(O)[O-];m1_m3:ClC1=CC(=C(NC(C)=O)C=C1)F, Reagents are:m1_m3:S(O)(O)(=O)=O, and Products are 0:ClC1=CC(=C(NC(C)=O)C=C1[N+](=O)[O-])F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4'-chloro-2'-fluoroacetanilide (51 g, 0.272 mol) in concentrated sulfuric acid (100 mL) is cooled to 0° C., treated with nitric acid (90% real, 14 mL, 0.300 mol) over 45 minutes, stirred for 10 minutes, and poured onto ice. The resultant aqueous mixture is filtered to obtain a tan solid which is washed with water, dried overnight, and recrystallized from a chloroform/hexanes (17:1) solution to give the title product as a yellow solid. |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1_m3_m4:ClC1=CC(=C(NC(C)=O)C=C1[N+](=O)[O-])F, Reagents are:m1_m3_m4:[Pt];m1_m3_m4:C(C)O.O1CCCC1, and Products are 0:NC=1C(=CC(=C(NC(C)=O)C1)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4'-chloro-2'-fluoro-5'-nitroacetanilide (35.2 g, 151 mmol), and 5% platinum on carbon (7.0 g, 20 wt/wt %) in an ethanol/tetrahydrofuran (2:1) solution is hydrogenated until 28 psi of hydrogen is taken up. The reaction mixture is then filtered, and concentrated in vacuo to give the title product as a tan solid which is identified by 1H NMR spectral analysis. |
Here is a chemical reaction formula: Reactants are:m7_m4:C(C#C)N;m1_m2_m5_m3_m6:NC=1C(=CC(=C(NC(C)=O)C1)F)Cl;m1_m2_m5_m3_m6:C(C)N(CC)CC;m1_m2_m5_m3_m6:C1(=CC=CC=C1)OC(=O)Cl, Reagents are:m8:O;m7_m4:O1CCCC1;m1_m2_m5_m3_m6:O1CCCC1;m1_m2_m5_m3_m6:O1CCCC1;m9:C(C)(=O)OCC, and Products are 0:C(C)(=O)NC=1C(=CC(=C(C1)NC(=O)NCC#C)Cl)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 5'-amino-4'-chloro-2'-fluoroacetanilide (11.25 g, 55.6 mmol), and triethylamine (7.70 mL, 55.6 mmol) in tetrahydrofuran is added dropwise to a stirred solution of phenylchloroformate (8.70 mL, 69.4 mmol) in tetrahydrofuran while maintaining the reaction mixture temperature at 25°-30° C. After the addition is complete, the reaction mixture is stirred at room temperature for 75 minutes, and poured into ethyl acetate. The organic mixture is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a tan solid. A solution of the solid in tetrahydrofuran is treated with propargylamine (9.52 mL, 139 mmol), refluxed for 1 hour, and poured into water. The aqueous mixture is filtered to obtain a solid which is washed sequentially with water, 0.5N hydrochloric acid and water, and dried overnight to give the title product as a beige solid. |
Here is a chemical reaction formula: Reactants are:m3:C(=NC(=O)Cl)=O;m4_m5:N1=CC=CC=C1;m4_m5:C(=NC(=O)Cl)=O;m1_m2_m6:C(C)(=O)NC=1C(=CC(=C(C1)NC(=O)NCC#C)Cl)F;m1_m2_m6:N1=CC=CC=C1, Reagents are:m1_m2_m6:C(Cl)Cl, and Products are 0:ClC1=CC(=C(NC(C)=O)C=C1N1C(N(C(NC1=O)=O)CC#C)=O)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-(5-acetamido-2-chloro-4-fluorophenyl)-3-(2-propynyl)urea (4.50 g, 15.9 mmol), and pyridine (2.56 mL, 31.8 mmol) in methylene chloride is treated with N-(chlorocarbonyl) isocyanate (1.92 mL, 23.9 mmol), stirred at room temperature overnight, refluxed for 90 minutes, cooled to room temperature, treated with additional pyridine (1.30 mL) and N-(chlorocarbonyl) isocyanate (1.92 mL), stirred for 10 minutes, cooled to room temperature, and filtered to obtain a solid. The solid is washed sequentially with water and hexanes, and dried to give the title product as a tan solid. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(=O)OCC;m1_m2_m5:ClC1=CC(=C(NC(C)=O)C=C1N1C(N(C(NC1=O)=O)CC#C)=O)F;m1_m2_m5:Cl;m4:[OH-].[Na+], Reagents are:m1_m2_m5:C(C)O, and Products are 0:NC=1C(=CC(=C(C1)N1C(N(C(NC1=O)=O)CC#C)=O)Cl)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4'-chloro-2'-fluoro-5'-[hexahydro-2,4,6-trioxo-3-(2-propynyl)-s-triazin-1-yl]acetanilide (3.00 g, 8.5 mmol), and 3N hydrochloric acid (25 mL) in ethanol (50 mL) is refluxed for 3 hours, cooled to room temperature, and poured into ethyl acetate. 3N sodium hydroxide solution (25 mL) is added to the organic solution, and the phases are separated. The organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, and concentrated in vacuo to give the title product as a beige solid (2.17 g, mp 118°-121° C.). |
Here is a chemical reaction formula: Reactants are:m3:ClC1=CC(=C(N)C=C1)F;m4:O.C(C)(=O)OCC;m1_m2_m6:ClC1=CC(=C(N)C=C1)F;m1_m2_m6:C1(C2=C(C(=O)O1)CCCC2)=O;m5:C(C)(=O)OCC, Reagents are:m1_m2_m6:C(C)(=O)O, and Products are 0:ClC1=CC(=C(C=C1)N1C(=O)C2=C(CCCC2)C1=O)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4-chloro-2-fluoroaniline (19.0 g, 130.6 mmol), and 3,4,5,6-tetrahydrophthalic anhydride (19.85 g, 130.6 mmol) in acetic acid (150 mL) is refluxed for 2 hours, treated with additional 4-chloro-2-fluoroaniline (3.0 g), refluxed for 90 minutes, stirred at room temperature overnight and poured into a water/ethyl acetate mixture. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a purple oil. Flash column chromatography of the oil using silica gel and 15% to 20% ethyl acetate in hexanes solutions gives the title product as an off-white solid (25.3 g, mp 81°-82° C.). |
Here is a chemical reaction formula: Reactants are:m2:[N+](=O)(O)[O-];m1_m3:ClC1=CC(=C(C=C1)N1C(=O)C2=C(CCCC2)C1=O)F, Reagents are:m1_m3:S(O)(O)(=O)=O, and Products are 0:ClC1=CC(=C(C=C1[N+](=O)[O-])N1C(=O)C2=C(CCCC2)C1=O)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of N-(4-chloro-2-fluorophenyl)-1-cyclohexene-1,2-dicarboximide (24.4 g, 86.7 mmol) in sulfuric acid (150 mL) is cooled to -3° C., treated dropwise with nitric acid (70% real, 6.70 mL, 104 mmol) while maintaining the temperature at 0°-2° C., stirred at room temperature for 90 minutes, and poured onto ice. The aqueous mixture is stirred for several minutes, and filtered to obtain a solid which is washed with water and dried to give the title product as a white powder (28.6 g, mp 152°-155° C.). |
Here is a chemical reaction formula: Reactants are:m4_m1_m3:ClC1=CC(=C(C=C1[N+](=O)[O-])N1C(=O)C2=C(CCCC2)C1=O)F;m2:C(C)(=O)OCC, Reagents are:m4_m1_m3:C(C)(=O)O;m4_m1_m3:[Fe], and Products are 0:NC=1C(=CC(=C(C1)N1C(=O)C2=C(CCCC2)C1=O)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Iron powder (7.30 g, 130.7 mmol) is added portionwise to a mixture of N-(4-chloro-2-fluoro-5-nitrophenyl)-1-cyclohexene-1,2-dicarboximide (10.6 g, 32.7 mmol) in acetic acid (100 mL) at 65° C. After the addition is complete, the reaction mixture is stirred for 10 minutes, and filtered through diatomaceous earth. The filtrate is concentrated in vacuo to obtain a dark solid. A mixture of the solid in an ethyl acetate/saturated sodium hydrogen carbonate solution is filtered through diatomaceous earth, and the phases are separated. The organic phase is washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a yellow solid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:NC=1C(=CC(=C(C1)N1C(N(C(N(C1=O)C)=O)CC(=O)OC(C)C)=O)Cl)F;m1_m2_m3:FC1=C2C(C(=O)OC2=O)=CC=C1, Reagents are:m1_m2_m3:C(C)(=O)O, and Products are 0:ClC1=C(C=C(C(=C1)F)N1C(C=2C(C1=O)=C(C=CC2)F)=O)N2C(N(C(N(C2=O)C)=O)CC(=O)OC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (1.0 g, 2.6 mmol) and 3-fluorophthalic anhydride (0.51 g, 3.1 mmol) in acetic acid is refluxed for 6 hours, stirred at room temperature for several days and poured onto ice. The resultant aqueous mixture is filtered to obtain a solid. The solid is dried and chromatographed (silica gel/2.5% ether in methylene chloride solution) to give the title product as a yellow foam, mp 119°-125° C. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m2_m3_m5:ClC1=C(C=C(C(=C1)F)N=C1SC(N2N1CCCC2)=O)N2C(N(C(NC2=O)=O)C)=O;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m5:C(C=C)Br, Reagents are:m1_m2_m3_m5:CC(=O)C, and Products are 0:C(C=C)N1C(N(C(N(C1=O)C)=O)C1=C(C=C(C(=C1)N=C1SC(N2N1CCCC2)=O)F)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-{2-chloro-4-fluoro-5-[(tetrahydro-3-oxo-1H,3H-[1,3,4]thiadiazolo[3,4-a]pyridazin-1-ylidene)-amino]phenyl}-3-methyl-s-triazine-2,4,6(1H,3H,5H)-trione (1.00 g, 2.27 mmol), potassium carbonate (0.627 g, 4.54 mmol) and allyl bromide (0.329 g, 2.72 mmol) in acetone is stirred overnight at 40° C. and poured into water. The aqueous mixture is extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a white glass (0.8 g) which is identified by NMR spectral analyses. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClC1=CC=C(C(=O)CCC(=O)O)C=C1;m1_m3_m2:O.NN, Reagents are:m1_m3_m2:C(C)O, and Products are 0:ClC1=CC=C(C=C1)C=1CCC(NN1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3-(4-chlorobenzoyl)propionic acid (20g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:ClC1=CC=C(C(=O)C(C(=O)O)C)C=C1;m1_m4_m2_m3:C(C)(=O)[O-].[Na+];m1_m4_m2_m3:Cl.C(C)(C)(C)NN, Reagents are:m1_m4_m2_m3:C(CCC)O, and Products are 0:ClC1=CC=C(C=C1)C=1CCC(N(N1)C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4-chlorobenzoylpropionic acid (4.24 g) in n-butanol (150 ml) was added anhydrous sodium acetate (1.54 g) and t-butylhydrazine hydrochloride (2.75 g) portionwise at room temperature. The resulting mixture was refluxed for 9 hours distilling off 65 ml of n-butanol during that time. The resulting mixture was cooled and poured into water (500 ml) and extracted with methylene chloride (3×150 ml). The combined organic layers were washed with 2% aqueous sodium hydroxide (3×100 ml), water (2×100 ml), 2% aqueous hydrochloric acid (3×100 ml), and water (1×100 ml), dried and evaporated under vacuum yielding 1.71 g of the expected product. |
Here is a chemical reaction formula: Reactants are:m2:[Cl-].[Al+3].[Cl-].[Cl-];m1_m4:CC1=CC=C(C(=O)CCC(=O)O)C=C1;m3:ClCl, Reagents are:m1_m4:C(Cl)Cl, and Products are 0:ClC=1C=C(C(=O)CCC(=O)O)C=C(C1C)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 3-(4-methylbenzoyl)propionic acid (7.5 g) and methylene chloride (250 ml) was added slowly portionwise aluminum chloride (15 g) at 0° C. After the addition was completed chlorine gas was bubbled in slowly at 0° C. After 6 hours the reaction mixture was poured into mixture of hydrochloric acid and ice and extracted with methylene chloride (3×150 ml), the combined organic layers were washed with water, dried and evaporated under vacuum yielding 3-(3,5-dichloro-4-methylbenzoyl)propionic acid as a yellow solid (4.5 g). |
Here is a chemical reaction formula: Reactants are:m2:O1CCCC=C1;m1:C(C#CCO)O, Reagents are:m4:CCOCC;m3:CCOCC, and Products are 0:O1C(CCCC1)OCC#CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 5.0 g of 2-butyne-1,4-diol and 10 milligrams of p-toluenesulfonic add and 150 ml of dry ether there was added dropwise with stirring at room temperature 4.9 g of 3,4-dihydro-2H-pyran. After stirring overnight at ambient temperature the ether was evaporated and the residue was poured into 200 ml of water. The aqueous solution was extracted with hexane (2×100 ml) and then re-extracted with ether (3×100 ml). The combined ether extracts were washed with 100 ml of brine, dried over magnesium sulfate and evaporated to yield 6.8 g of 4-tetrahydropyranoxy-2-butyn-1-ol. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClC1=CC=C(C=C1)C=1CCC(NN1)=O;m1_m2_m3:C(C)(=O)O;m1_m2_m3:BrBr, Reagents are:m4:O, and Products are 0:ClC1=CC=C(C=C1)C=1C=CC(NN1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone. |
Here is a chemical reaction formula: Reactants are:m2_m3:O;m2_m3:Cl;m1_m4_m5:ClC1(C(C(C1)(F)F)(F)Cl)Cl, Reagents are:m1_m4_m5:CCOCC;m1_m4_m5:C(C)N(CC)CC, and Products are 0:ClC1(C(C=C1Cl)(F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1,1,2 trichloro-2,3,3-trifluorocyclobutane (55.5 g) in 100 ml of anhydrous ether, triethylamine (40 ml) was added dropwise over 30 min at room temperature, and the mixture was stirred overnight at ambient temperature. The mixture was then stirred with 120 ml H2O and 7.5 ml of concentrated HCl. The ether layer was washed with H2O (100 ml), brine (100 ml), dried over anhydrous MgSO4, and evaporated in vacuo. The residue was distilled fractionally atmospheric pressure from 64°-68° C. to yield 36 g (79%) of a colorless liquid as pure product. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClC(C(C(=O)O)(F)F)(C(=O)O)F, Reagents are:m1_m2_m3:O1CCOCC1;m1_m2_m3:[Zn], and Products are 0:FC(C(=O)O)(C(C(=O)O)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirring solution of the chlorotrifluorosuccinic acid (part b) (24.5 g) in 200 ml dioxane was added portionwise zinc metal (85 g) and the mixture was stirred at ambient temperature for 10 hours to yield a viscous liquid which was decanted from the unreacted zinc. Most of the dioxane was evaporated in vacuo. The residue was dissolved in 100 ml H2O and a solution of 7.7 ml of concentrated H2SO4 in 25 ml of water was added. The solution was extracted with ether (3×100 ml) and dried over anhydrous MgSO4. The organic layer was stripped to yield 8.3 g (32%) of the product as a crystalline solid. |
Here is a chemical reaction formula: Reactants are:m1_m4_m3:C(C1=CC=CC=C1)(=O)CCCC(=O)O;m1_m4_m3:NN;m2:O, Reagents are:m1_m4_m3:C1(=CC=CC=C1)C;m6:C1(=CC=CC=C1)C;m5:CCOCC, and Products are 0:C1(=CC=CC=C1)C1=CC=CC(N=N1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 10 g (0.052 mole) of 4-benzoylbutyric acid in 300 ml of toluene, hydrazine was added in one portion and the reaction was heated to reflux until all water had ceased to azeotrope. The reaction mixture was cooled and the toluene was stripped off in vacuo. The residue was dissolved in 200 ml Et2O and washed with H2O (100 ml) and brine (100 ml). The ether extract was dried over anhydrous MgSO4, filtered and stripped to yield an orange semisolid which was triturated with ether to yield 3.8 g (39%) of the desired product as a yellow solid. |
Here is a chemical reaction formula: Reactants are:m3:[H][H];m4:COC(OC)=O;m1_m6_m2_m5:[H-].[Na+];m1_m6_m2_m5:ClC=1C=C2CCC(C2=CC1)=O, Reagents are:m1_m6_m2_m5:C(OC)COC;m1_m6_m2_m5:C(OC)COC, and Products are 0:C(=O)(OC)C1C(C2=CC=C(C=C2C1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of sodium hydride (2.4 g, 60% in mineral oil, 0.06 mole) and 50 ml dry dimethoxyethane, 5-chloroindanone (50 g, 0.03 mole) in 50 ml dimethoxyethane was added dropwise at room temperature. The mixture was stirred at room temperature until hydrogen evolution ceased. Then dimethylcarbonate (27 g, 0.3 mole) was added dropwise at room temperature and the reaction was heated to 60° C. for one hour. The reaction was cooled to room temperature, quenched with 100 ml H2O, acidified to pH 5 with concentrated HCl and extracted with ethyl ether (3×100 ml). The ether extract was washed with brine (100 ml), dried over anhydrous MgSO4 and stripped to yield 3.0 g (45%) of the desired product as a tan solid. |
Here is a chemical reaction formula: Reactants are:m1:P(=O)(Cl)(Cl)Cl;m4:C([O-])([O-])=O.[K+].[K+];m3:ClC1=CC=C(C=C1)CC(=O)O;m2:CN(C)C=O, Reagents are:m5:C1(=CC=CC=C1)C, and Products are 0:ClC1=CC=C(C=C1)C(C=O)=CN(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Phosphorus oxychloride (92 g) was added dropwise to stirred DMF (78 ml) between 10°-15° C. To the resulting slurry was added 4-chlorophenylacetic acid (34.12 g). The resulting mixture was stirred at room temperature for one half hour and then heated to 70°-80° C. during 5.5 hours, during which time the mixture became effervescent. The reaction mixture was cooled and poured slowly onto cracked ice. The resulting suspension was brought to pH 10 with solid potassium carbonate. Ice was added intermittently during this addition to maintain the temperature below 15° C. Toluene (150 ml) was added and the resulting mixture heated at 100° C. for one hour. The mixture was cooled and allowed to stand overnight. The two resulting layers were separated and the aqueous layer extracted with toluene (2×100 ml). The combined organic layers were washed with water (5×200 ml) and dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo and the resulting yellow solid was triturated with hexane to yield 26 g of 2-(4-chlorophenyl)-3-dimethylaminopropenal as a tan solid mp. 120°-125° C. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:C[O-].[Na+];m1_m5_m2:C(#N)CC(=O)N;m3:ClC1=CC=C(C=C1)C(C=O)=CN(C)C;m4:CC(=O)OCC1=C2C=CC=CC2=C(C3=CC=CC=C31)COC(=O)C, Reagents are:m1_m5_m2:CO;m6:O, and Products are 0:C(#N)C=1C(NC=C(C1)C1=CC=C(C=C1)Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic add (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone. |
Here is a chemical reaction formula: Reactants are:m2:N1C(C=CC2=CC=CC=C12)=O;m4:[Cl-].[NH4+];m3:BrCC#CCC;m1_m5:[H-].[Na+], Reagents are:m1_m5:CN(C)C=O;m6_m0:CCCCCC, and Products are 0:ClC1=C2C=CC(N(C2=CC=C1)CC#CCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 700 mg) in dry DMF (100 ml) at 0° C. was added the preceding quinolinone (2.05 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (1.6 g) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid (1 g). |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[NH4+];m1_m2_m3_m6_m5:ClC1=CC=C(C=C1)C(C=O)=CN(C)C;m1_m2_m3_m6_m5:NC(=O)N;m1_m2_m3_m6_m5:Cl, Reagents are:m1_m2_m3_m6_m5:C(C)O;m1_m2_m3_m6_m5:O, and Products are 0:ClC1=CC=C(C=C1)C=1C=NC(NC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-(4-chlorophenyl)dimethylaminopropenal (Example 145a) (5.13 g), urea (2.4 g), concentrated HCl (10 ml), water (4 ml) and ethanol (150 ml) was refluxed for 4 hours. After cooling to room temperature concentrated ammonium chloride was added until the pH was 7. The resulting yellow solid was filtered off and dried yielding 1.5 g of 5-(4-chlorophenyl)-2-pyrimidinone. |
Here is a chemical reaction formula: Reactants are:m1_m6:[H-].[Na+];m4:[Cl-].[NH4+];m2:N1C(C=CC=C1)=O;m5_m0:CCCCCC;m3:BrCC#CCC, Reagents are:m1_m6:CN(C)C=O, and Products are 0:ClC1=CC=C(C=C1)C=1C=NC(N(C1)CC#CCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of NaH (60% in mineral oil, 340 mg) in dry DMF (75 ml) at 0° C. was added the preceding pyridinone (1.0 g) and the mixture was stirred at 0° C. for one half hour. To the resulting suspension was added 1-bromo-2-pentyne (750 mg) dropwise. The resulting mixture was kept at 0° C. for one half hour and poured into saturated aqueous ammonium chloride (200 ml). The aqueous suspension was extracted with ether (3×100 ml), the combined ether layers washed with brine and dried, yielding the crude product. Trituration with hexane yielded the product as a yellow solid. |