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Here is a chemical reaction formula: Reactants are:m1_m2_m3:C=C1CC(=O)O1.CC(=O)C;m1_m2_m3:N1CCCC1, Reagents are:m1_m2_m3:C1(=CC=CC=C1)C, and Products are 0:O=C(CC(=O)N1CCCC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 9 ml (0.05 mol) of diketene-acetone adduct and a solution of 4.2 ml (0.05 mol) of pyrrolidine in 20 ml of toluene were treated as described in preparation 7. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→1%) yielding 7.6 g of the title compound as a dark oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(CC(=O)C)(=O)NC1=CC=CC=C1;m1_m2_m4_m3:[OH-].[Na+];m1_m2_m4_m3:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m4_m3:O, and Products are 0:C1(=CC=CC=C1)NC(C(C(C)=O)=NNC1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.5 g (25.4 mmol) of acetoacetanilide, a solution of 3.46 g (89 mmol) of NaOH in 45 ml of water and 95 mmol of phenyldiazonium chloride were treated as described in preparation 8. The residue was crystallised from EtOH, yielding 3.4 g of the title compound. M.p.=96°-97° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C=C1CC(=O)O1.CC(=O)C;m1_m3_m2:CNC, Reagents are:m1_m3_m2:C1(=CC=CC=C1)C, and Products are 0:CN(C(CC(C)=O)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 9 ml (0.05 mmol) of diketene-acetone adduct in 20 ml of toluene was treated with gaseous dimethylamine at room temperature until the reaction was complete. The solvent was removed in vacuo and the residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→10%) yielding 7.0 g of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:CN(C(CC(C)=O)=O)C;m1_m2_m4_m3:[OH-].[Na+];m1_m2_m4_m3:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m4_m3:O, and Products are 0:CN(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.5 g (0.035 mol) of N,N-dimethyl-3-oxobutyramide, a solution of 4.9 g (0.122 mol) of NaOH in 45 ml of water and 0.037 mol of phenyldiazonium chloride were treated as described in preparation 8. The crude reaction mixture was purified by chromatography on silica gel (hexane/Et2O 0%→100%) obtaining 3.5 g of the title compound which was used as such in the subsequent step. M.p.=131°-133° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)(C)N(C(CC(C)=O)=O)C(C)C;m1_m2_m4_m3:[OH-].[Na+];m1_m2_m4_m3:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m4_m3:O, and Products are 0:C(C)(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.0 g (0.038 mol) of N,N-diisopropyl-3-oxobutyramide, a solution of 5.3 g (0.133 mol) of NaOH in 58 ml of water and 0.04 mol of phenyldiazonium chloride were treated as described in preparation 8. The crude reaction mixture was purified by chromatography on silica gel (hexane/Et2O 95:5) obtaining 7.5 g of the title compound which was used as such in the subsequent step. M.p.=143°-145° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5_m4:CCOC(=O)CC(=O)C(F)(F)F;m1_m2_m3_m5_m4:CC(=O)O[Na];m1_m2_m3_m5_m4:O;m1_m2_m3_m5_m4:[Cl-].C1(=CC=CC=C1)[N+]#N, Reagents are:m1_m2_m3_m5_m4:C(C)O, and Products are 0:C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C(F)(F)F)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.3 ml (0.05 mol) of ethyl 3-oxo-4,4,4-trifluoroacetoacetate, 6 g (0.073 mol) of CH3COONa, 20 ml of water, 37.5 ml of ethanol and a solution of 0.05 mol of phenyldiazonium chloride were treated as described in preparation 2. The crude product was purified by chromatography on silica gel (hexane/Et2O 0%→25%) obtaining 8.65 g of the title compound. M.p.=78°-80° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m4_m3:CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C;m1_m2_m4_m3:C(=C)OC(=O)Cl, Reagents are:m1_m2_m4_m3:ClCCCl, and Products are 0:Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.2 g (4.2 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline and 1.8 g (12.6 mmol) of proton sponge in 34 ml of 1,2-dichloroethane was treated with 1.4 ml (16.8 mmol) of vinylchloroformate at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at this temperature for 15 min and then refluxed for 3 h, the solvent was removed in vacuo, the residue was taken up in water and extracted with Et2O. The organic layer was washed with 3% HCl, then was dried over Na2SO4 and the solvent was removed in vacuo. The dark residue was dissolved in EtOH, 3 ml of concentrated HCl were added and the solution refluxed for 3 hours. The solvent was removed in vacuo, obtaining 0.88 g of the title compound which was used as such in the subsequent step. M.p.=90° C. dec. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O;m1_m2_m3_m4_m5:C1(CC1)CBr;m1_m2_m3_m4_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4_m5:[I-].[K+], Reagents are:m1_m2_m3_m4_m5:CN(C)C=O, and Products are 0:Cl.C1(CC1)CN1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.88 g (3.08 mmol) of (±)-trans-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.44 g (3,23 mmol) of cyclopropylmethyl bromide, 0.64 g of potassium carbonate and a catalytical amount of potassium iodide in 15.4 ml of DMF were stirred at 60° C. for 2 h. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 90:10:0.8). The solid product was dissolved in acetone and the solution brought to acidic pH with HCl/Et2O. The precipitate was filtered, yielding 0.28 g of the title compound. M.p.=78° C. dec. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.COC=1C=C(C=CC1)[C@@]12CCNC[C@@H]2CCC(C1)=O;m1_m2_m3_m4_m5:C(CCC)Br;m1_m2_m3_m4_m5:C([O-])([O-])=O.[K+].[K+];m1_m2_m3_m4_m5:[I-].[K+], Reagents are:m1_m2_m3_m4_m5:CN(C)C=O, and Products are 0:C(CCC)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.71 g (2.55 mmol) of (±)-trans-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8, 8a-decahydroisoquinoline hydrochloride, 0.37 g (2.68 mmol) of butyl bromide, 0.53 g of potassium carbonate and a catalytical amount of potassium iodide in 15 ml of DMF were reacted as described in preparation 20, yielding 0.2 g of the title compound which was used as such in the subsequent step. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m4_m3:C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C)=O;m1_m2_m4_m3:CC(=O)O[Na], Reagents are:m1_m2_m4_m3:C(C)(=O)O;m5:[Zn], and Products are 0:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.8 g (2.47 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride and 0.87 g (93.7 mmol) of ethyl 2-phenylhydrazono-3-oxobutyrate [Organic Reactions, R. Adams Ed; Wiley, New York, 10, 32-33, (1951-1959)] were dissolved in a mixture of 3 mi of glacial acetic acid and 0.34 g (4.2 mmol) of CH3COONa. The solution was treated as described in example 1 adding 0.74 g (11.3 mmol) of zinc dust. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 94:5:0.5; Rf=0.3), obtaining 0.6 g of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)OCC;m1_m2:B(Br)(Br)Br, Reagents are:, and Products are 0:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.6 g (1.5 mmol) of (±)-trans-6-ethyl-2-ethoxycarbonyl-3-methyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.84 ml (9.0 mmol) of boron tribromide as described in example 2. The crude solid was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 80:20:2), yielding 0.12 g of the title compound. M.p.=195°-197° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m4_m5:C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC;m1_m2_m3_m4_m5:CC(=O)O[Na], Reagents are:m1_m2_m3_m4_m5:[Zn];m1_m2_m3_m4_m5:C(C)(=O)O, and Products are 0:C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3 g (9.3 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.92 g (11.2 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.92 g (11.2 mmol) of CH3COONa, 2.8 g (42.8 mmol) of zinc dust and 9.3 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography (AcOEt/MeOH/conc. NH4OH 90:10:1; Rf=0.27) yielding 0.56 g of the title compound. M.p. (.HCl)=250° C. dec. C25H35N3O2I.R. (KBr) (hydrochloride): 3410, 3200, 2915, 2510, 1605, 1580 cm-1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C(C)N1C[C@@H]2CC(CC[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m4_m5:C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC;m1_m2_m3_m4_m5:CC(=O)O[Na], Reagents are:m1_m2_m3_m4_m5:[Zn];m1_m2_m3_m4_m5:C(C)(=O)O, and Products are 0:C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)OC)C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.9 g (2.9 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-7-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride (J. Med. Chem., 35, 48, 1992), 0.9 g (3.5 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.28 g (3.5 mmol) of CH3COONa, 0.87 g (13.3 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4 OH 86: 10:0.6; Rf=0.27), to yield 0.2 g of the title compound.M.p.=153°-155° C. dec. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)OC)C)CC;m1_m2:B(Br)(Br)Br, Reagents are:, and Products are 0:C(C)N(C(=O)C1=C(C=2C[C@]3(CCN(C[C@@H]3CC2N1)C)C1=CC(=CC=C1)O)C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.29 g (0.71 mmol) of (±)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline were treated with 0.4 ml (4.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4OH 80:12:0.8). The crude product was triturated with a mixture of acetone/MeOH=3:2, yielding 0.14 g of the title compound. M.p.=235°-238 l ° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CC=CC=C1)NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)OC)N1)C;m1_m2:B(Br)(Br)Br;m3:Cl.CCOCC, Reagents are:m4:CO, and Products are 0:Cl.C(C1=CC=CC=C1)NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)C)C2=CC(=CC=C2)O)N1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.38 g of (±)-trans-2-benzylaminocarbonyl-3,6-dimethyl-8a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.55 ml (5.7 mmol) of boron tribromide as described in example 2. The residue was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallised from a mixture of acetone/MeOH=1:1, yielding 0.15 g of the title compound. M.p.=297°-299° C. C27H31N3 O2.HCl I.R. (KBr): 3290, 2910, 1650, 1540, 1320cm-1 |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C1(CC1)CN1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m4_m5:C(C)N(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)CC;m1_m2_m3_m4_m5:CC(=O)O[Na], Reagents are:m1_m2_m3_m4_m5:[Zn];m1_m2_m3_m4_m5:C(C)(=O)O, and Products are 0:Cl.C1(CC1)CN1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)N(CC)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.28 g (0.80 mmol) of (±)-trans-2-cyclopropylmethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 0.56 g (2.14 mmol) of N,N-diethyl-2-phenylhydrazono-3-oxobutyramide, 0.131 g (1.6 mmol) of CH3COONa, 0.402 g (6.16 mmol) of zinc dust and 10 ml of glacial acetic acid were treated as described in example 1. The residue was purified by flash chromatography ((i-Pr)2O/MeOH/conc. NH4OH 90:10:0.5). The product was dissolved in acetone and the solution brought to acidic pH with Et2O/HCl . The solid was filtered, washed and dried yielding 0.225 g of the title compound. M.p.=190°-195° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5_m4:Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m5_m4:C1(=CC=CC=C1)NN=C(C(=O)N)C(C)=O;m1_m2_m3_m5_m4:CC(=O)O[Na];m1_m2_m3_m5_m4:C(C)(=O)O, Reagents are:m1_m2_m3_m5_m4:[Zn], and Products are 0:NC(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.24 g (10 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 6.16 g (30.0 mmol) of 2-phenylhydrazono-3-oxobutyramide, 2.46 g (7.0 mmol) of CH3COONa, 7.85 g (120.0 mmol) of zinc dust and 15 ml of glacial acetic acid were treated as described in example 1. The residue was purified by chromatography on silica gel (Et2O-EtOAc/MeOH 0%→50%) yielding 3.0 g of oily product which was triturated in Et2O yielding 2.5 g of the title compound. M.p.=176°-178° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m4_m5:C1(=CC=CC=C1)NN=C(C(=O)OCC)C(C(F)(F)F)=O;m1_m2_m3_m4_m5:CC(=O)O[Na], Reagents are:m1_m2_m3_m4_m5:[Zn];m1_m2_m3_m4_m5:C(C)(=O)O, and Products are 0:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C(F)(F)F)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.24 g (10 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 8.65 g (30 mmol) of ethyl 2-phenylhydrazono-4,4,4-trifluoro-3-oxobutyrate, 2.46 g (30 mmol) of CH3COONa, 7.85 g (120 mmol) of zinc dust and 15 ml of glacial acetic acid were treated as described in example 1. The residue was purified by chromatography on silica gel EtOAc/MeOH 0%→10%) yielding 3.0 g of product which was triturated in Et2O yielding 2.5 g of the title compound. M.p. 209°-211° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C(C)N1C[C@@H]2CCC(C[C@]2(CC1)C1=CC(=CC=C1)OC)=O;m1_m2_m3_m4_m5:CN(C(C(C(C)=O)=NNC1=CC=CC=C1)=O)C;m1_m2_m3_m4_m5:CC(=O)O[Na], Reagents are:m1_m2_m3_m4_m5:[Zn];m1_m2_m3_m4_m5:C(C)(=O)O, and Products are 0:CC1=CNC=2CC3CCNCC3CC21, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g (3.1 mmol) of (±)-trans-2-ethyl-4a-(3-methoxyphenyl)-6-oxo-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline hydrochloride, 2.33 g (10 mmol) of N, N-dimethyl-2-phenylhydrazono-3-oxobutyramide, 0.82 g (1 0 mmol) of CH3COONa, 2.6 g (40 mmol) of zinc dust and 5 ml of glacial acetic acid were treated as described in example 1. The residue was purified by chromatography on silica gel (EtOAc/MeOH 0%→30%) yielding 0.5 g of product which was crystallized from Et2O yielding 0.5 g of the title compound. M.p.=151°-153° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:CN(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)OC)N1)C)C;m1_m2:B(Br)(Br)Br;m3:Cl.CCOCC, Reagents are:m4:CO, and Products are 0:Cl.CN(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC)C2=CC(=CC=C2)O)N1)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.5 g (1.25 mmol) of (±)trans-2-dimethylaminocarbonyl-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g] isoquinoline were treated with 0.725 ml (7.5 mmol) of boron tribromide as described in example 2. The etude product was dissolved in MeOH and the solution brought to acidic pH with HCl/Et2O. The solvent was evaporated in vacuo and the solid crystallized from EtOH, yielding 0.15 g of the title compound. M.p.=305° C. dec. |
Here is a chemical reaction formula: Reactants are:m6:Cl;m3:C(#N)[BH3-].[Na+];m8_m4_m5:O1C(=CC=C1)C=O;m8_m4_m5:C(#N)[BH3-].[Na+];m1_m9_m2_m7:C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCNC[C@H]3C2)C2=CC(=CC=C2)OC)N1)C)CC;m1_m9_m2_m7:O1C(=CC=C1)C=O, Reagents are:m8_m4_m5:C(C)(=O)O;m1_m9_m2_m7:CO;m1_m9_m2_m7:C(C)(=O)O, and Products are 0:Cl.C(C)N(C(=O)C1=C(C2=C(C[C@@]3(CCN(C[C@H]3C2)CC=2OC=CC2)C2=CC(=CC=C2)OC)N1)C)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.3 g (3.3 mmol) of (±)-trans-2-diethylaminocarbonyl-8a-(3-methoxyphenyl)-3-methyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline, 0.28 ml (4.95 mmol) of acetic acid, 0.33 ml (3.96 mmol) of 2-furaldehyde were dissolved in 50 ml of MeOH under nitrogen atmosphere. 0.415 g (6.6 mmol) of sodium cyanoborohydride were added and the solution stirred for 15 h. Additional acetic acid (0.1 ml), 2-furaldehyde (0.3 ml) and sodium cyanoborohydride (0.2 g) were added. After two hours of stirring the reaction mixture was cooled to 0° C. and 50 ml of 5N hydrochloric acid were added. The solvent was removed in vacuo, the aqueous solution was extracted with Et2O, the pH was adjusted to 8 with 20% NaOH and then extracted with AcOEt. The organic layer was dried over Na2SO4 and the solvent was removed in vacuo. The crude product was dissolved in acetone/MeOH and the solution brought to acidic pH with HCl/Et2O . The precipitate was filtered, yielding 1.7 g of the title compound. M.p.=105° C. dec. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)OC)NC(=C3C)C(=O)N3CCCC3;m1_m2:B(Br)(Br)Br, Reagents are:, and Products are 0:C(C)N1C[C@H]2CC3=C(C[C@@]2(CC1)C1=CC(=CC=C1)O)NC(=C3C)C(=O)N3CCCC3, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.63 g (1.37 mmol) of (±)-trans-6-ethyl-8a-(3-methoxyphenyl)-3-methyl-2-pyrrolidinocarbonyl-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[2,3-g]isoquinoline were treated with 0.77 ml (8.22 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (EtOAc/MeOH/conc. NH4OH 80:20:0.5). The resulting solid was triturated with Et2O, yielding 0.13 g of the title compound. M.p.=224°-226° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1CO)C)=O;m1_m2:C(C)#N.C(Cl)(Cl)(Cl)Cl.O;m3_m6:I(=O)(=O)(=O)[O-].[Na+];m4_m5:ClCCl, Reagents are:m3_m6:[Ru](Cl)(Cl)Cl;m4_m5:[Cl-].[Na+].O, and Products are 0:C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1C(=O)O)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (3R,5S)-1-t-butoxycarbonyl-5-hydroxymethyl-3-methylpyrrolidine-2-one in a solvent mixture of acetonitrile:carbon tetrachloride:water (2:2:3, 266 mL) was added sodium periodate (3 eq, 24.0 g) and ruthenium trichloride (2.2 mol %, 0.174 g). The solution was stirred 2 hr at room temperature and then diluted by the addition of dichloromethane (500 mL) and brine (200 mL). The organic phase was separated and the aqueous phase was extracted with dichloromethane (3 x 200 mL). The combined organic phases were dried over Na2SO4 then celite added. The solution was filtered under suction through a bed of celite and the filtrate was evaporated to give an oily residue which was crystallized in ethyl acetate and hexane to give 5.03 g product (54%). The mother liquor was purified by flash column chromatography on silica gel, eluting with 70% ethyl acetate in hexane (with 1% of formic acid) to give an additional 1.21 g (13%) of the acid (total 67% yield in two steps). 1H NMR (200 MHz, CDCl3): δ 6.65 (br s, 1H), 4.60 (d, J=8.6, 0.9 Hz, 1H), 2.70 (m, 1H), 2.40 (dd, J=12.5, 8.8 Hz, 1H), 2.0 (m, 1H), 1.55 (s, 9H), 1.25 (d, J=7.0 Hz, 3H). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(C)(C)(C)OC(=O)N1C([C@@H](C[C@H]1C(=O)O)C)=O;m1_m4_m2_m3:O.[OH-].[Li+];m1_m4_m2_m3:O, Reagents are:m1_m4_m2_m3:C1CCOC1;m5:C1CCOC1, and Products are 0:C(C)(C)(C)OC(=O)N[C@@H](C[C@H](C(=O)O)C)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of (3R,5S)-1-t-Butoxycarbonyl-5-carboxy-3-methylpyrrolidine-2-one (6.2 g, 25.5 mmol) in THF (50 mL) was treated with lithium hydroxide monohydrate (3 eq, 3.20 g) and water (5 mL). After stirring for 16 hr at room temperature the THF was removed in vacuo and water (20 mL) was added. The pH was adjusted to 3 by the addition of glacial acetic acid, ether (100 mL) was added and the layers separated. The aqueous phase was extracted with ether (3 x 100 mL) and the combined organic phases were washed with brine (400 mL), dried over Na2SO4, filtered and evaporated to dryness, azeotroping with toluene (3 x 15 mL). The residue was dried under high vacuum to give 6.58 g of the product (99%) as a white foam which was used without further purification: Rf 0.8 (1% formic acid in ethyl acetate, developed with ninhydrin). 1H NMR (200 MHz, D2O): δ 3.80 (dd, J=10.4, 4.7 Hz, 1H), 2.45 (m, 1H), 2.0 (m, 1H), 1.60 (ddd, J=12.8, 4.2, 10.3 Hz, 1H), 1.25 (s, 9H), 1.0 (d, J=7.0 Hz, 3H). |
Here is a chemical reaction formula: Reactants are:m4:CC1=C(C(=O)Cl)C=C(C(=C1)C1C=CCC1)S(=O)(=O)C;m1_m2_m3_m7:NC(=N)N;m1_m2_m3_m7:[Cl-].NC(=[NH2+])N;m1_m2_m3_m7:[Na];m5_m6:CC1C(C(=O)OC)=CC(=C(C1=S(=O)=O)Br)C;m5_m6:C1=CCCC1, Reagents are:m1_m2_m3_m7:COCCOC, and Products are 0:NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A fresh guanidine solution prepared from 5.6 g of guanidinium chloride and 1.6 g of sodium in 40 ml of ethylene glycol dimethyl ether is added to a solution of 1.2 g of 2-methyl-4-(1-cyclopentene-3-yl)-5-methylsulfonylbenzoyl chloride [obtainable by reaction of methyl 2-methyl-4-bromo-5-methyl-sulfonyl-benzoate with cyclopentene in the presence of Pd(II)acetate and tri-o-tolylphosphine, separation of the two isomers by means of a Prebar® stainless steel cartridge 250-50, filled with LiChroprep RP-18; eluent 0.1 m NaH2PO4 buffer/acetonitrile 9:1 with an increasing gradient to 1:1, and subsequent hydrolysis and conversion into the acid chloride with SOCl2 ], in 20 ml of ethylene glycol dimethyl ether with ice-cooling and the mixture is stirred at room temperature for 2 hours. The reaction mixture is then poured onto ice-water, acidified and washed with ethyl acetate and the pH of the solution is adjusted to 10. Customary working-up gives N-diaminomethylene-2-methyl-4-(1-cyclopentene-3-yl)-5-methylsulfonylbenzamide, which can be recrystallized from acetonitrile/diethyl ether, melting point 212°-214°. |
Here is a chemical reaction formula: Reactants are:m3:CS(=O)(=O)O;m2_m4:NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N, Reagents are:m2_m4:CC(=O)C, and Products are 0:NC(=NC(C1=C(C=C(C(=C1)S(=O)(=O)C)C1C=CCC1)C)=O)N;0:CS(=O)(=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: 700 mg of N-diaminomethylene-2-methyl-4-(1-cyclopenten-3-yl)-5-methylsulfonylbenzamide [which can be prepared according to Example 1; m.p. 212°-214°] are dissolved in 20 ml of acetone, and 6.1 ml of methanesulfonic acid are added, while stirring. Filtration and lyophilization give N-diaminomethylene-2-methyl-4-(1-cyclopenten-3-yl)-5-methylsulfonylbenzamide, methane-sulfonate, m.p. 202°-204°. |
Here is a chemical reaction formula: Reactants are:m1_m2:CS(=O)(=O)C=1C=C(C(=O)Cl)C=CC1C1C=CCC1;m1_m2:NC(=N)N, Reagents are:, and Products are 0:NC(=NC(C1=CC(=C(C=C1)C1C=CCC1)S(=O)(=O)C)=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Analogously to Example 1, by reaction of 2.2 g of 3-methylsulfonyl-4-(1-cyclopenten-3-yl)-benzoyl chloride with guanidine, customary working up gives N-diaminomethylene-3-methylsulfonyl-4-(1-cyclopenten-3-yl)benzamide, which can be recrystallized from acetonitrile/diethylether, m.p. 188°-190°. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1OC)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m3:[Zn];m1_m2:C(C)(=O)O, and Products are 0:NC=1C=C(C=CC1OC)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 700 mg of (Z)-1-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 35 ml of acetic acid, and 7 g of zinc were added thereto and stirred for one hour. The reaction liquid was filtered, concentrated and purified by silica gel column chromatography (dichloromethane:hexane=2:1 by volume) to obtain 314 mg of the intended compound. The yield was 49.3%. |
Here is a chemical reaction formula: Reactants are:m6_m3:[H-].[Na+];m4:[Cl-].[Na+];m1_m2_m5:[N+](=O)([O-])C=1C=C(C=O)C=CC1Cl;m1_m2_m5:[Br-].COC=1C=C(CP(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C1OC)OC, Reagents are:m7:C(C)(=O)O;m6_m3:C1=CC=CC=C1;m1_m2_m5:C1=CC=CC=C1, and Products are 0:[N+](=O)([O-])C=1C=C(C=CC1Cl)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of 3-nitro-4-chlorobenzaldehyde and 2.8 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 260 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with acetic acid, saturated sodium chloride solution was added thereto, and the resulting liquid was extracted with dichloromethane. The extract was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography diethyl (ether:hexane--1:2 by volume) to obtain 0.95 g of the intended compound. The yield of the product was 50.4%. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[Na+];m1_m2_m5:[N+](=O)([O-])C=1C=C(C=O)C=CC1C;m1_m2_m5:[Br-].COC=1C=C(CP(C2=CC=CC=C2)(C2=CC=CC=C2)C2=CC=CC=C2)C=C(C1OC)OC;m6_m3:[H-].[Na+], Reagents are:m7:C(C)(=O)O;m1_m2_m5:C1=CC=CC=C1;m6_m3:C1=CC=CC=C1, and Products are 0:[N+](=O)([O-])C=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g of 3-nitro-4-methylbenzaldehyde and 3.3 g of 3,4,5-trimethoxybenzyltriphenylphosphine bromide were dissolved in 50 ml of benzene, and a benzene solution containing 302 mg of sodium hydride dispersed therein was added thereto and reacted for 15 hours at room temperature. The reaction liquid was neutralized with acetic acid, saturated sodium chloride solution was added thereto, and the resulting liquid was extracted with dichloromethane. The extract was dried with anhydrous sodium sulfate, concentrated and then purified by silica gel column chromatography (diethyl ether:hexane=1:2 by volume) to obtain 0.99 g of the intended compound. The yield of the product was 47.8%. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m3_m4:ClCCl;m3_m4:[Zn];m1_m2:C(C)(=O)O, and Products are 0:NC=1C=C(C=CC1C)\C=C/C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 65 mg of (Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 4 ml of acetic acid and 4 ml of dichloromethane, and 300 mg of zinc were added thereto and stirred for one hour. The reaction liquid was filtered, concentrated and purified by silica gel column chromatography (dichloromethane:hexane=2.1 by volume) to obtain 29 mg of the intended compound. The yield was 46.5%. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1OC)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m1_m2:C(C)#N, and Products are 0:[N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.0 g of (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile were dissolved in 500 ml of acetonitrile and exposed to visible light rays for 60 minutes. The reaction liquid was concentrated and crystallized from ethyl acetate to obtain 996 mg of the intended compound. The yield was 49%. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m3:[Zn];m1_m2:C(C)(=O)O, and Products are 0:NC=1C=C(C=CC1OC)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 500 mg of (E)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile were dissolved in 25 ml of acetic acid, and 5 g of zinc were added thereto and stirred for 30 minutes at room temperature. The reaction liquid was filtered and then concentrated. The concentrated liquid was purified by silica gel column chromatography (ethyl acetate:hexane--1.2 by volume) to obtain 457 mg of the intended compound. The yield was 99%. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1C)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m1_m2:CC(=O)C, and Products are 0:[N+](=O)([O-])C=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.38 g of (Z)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 500 ml of acetone and the mixture was reacted in a photochemical apparatus (visible light) for 1 hour. The reaction mixture was concentrated and a quarter of it was purified on a silica gel plate to give 100 mg of the intended compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m3:[Zn];m1_m2:C(C)(=O)O, and Products are 0:NC=1C=C(C=CC1C)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 84 mg of (E)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for 1 hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 60 mg of the intended compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1Cl)\C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m1_m2:CC(=O)C, and Products are 0:[N+](=O)([O-])C=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.5 g of (Z)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 500 ml of acetone and the solution was reacted in a photochemical apparatus (visible light) for 1 hour. The reaction mixture was concentrated and a half of it was purified on a silica gel plate to give 400 mg of the intended compound. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, Reagents are:m3:[Zn];m1_m2:C(C)(=O)O, and Products are 0:NC=1C=C(C=CC1Cl)/C=C(/C#N)\C1=CC(=C(C(=C1)OC)OC)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: (E)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 330 mg was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for one hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 102 mg of desired product (yield 33%). |
Here is a chemical reaction formula: Reactants are:m2:[H][H];m1:C(C1=CC=CC=C1)OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OCC1=CC=CC=C1)=O, Reagents are:m4:[Ni];m3:C(C)O, and Products are 0:OC1=CC(OC(=C1)CC(O)C1=CC(=C(C=C1)O)O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 35.6 g (66.6 mmol) 4-benzyloxy-6-[2-[3,4-dibenzyloxyphenyl)-2-hydroxy-ethyl)]-2H-pyran-2-one (VI) was hydrogenated for 6 hours at room temperature under a hydrogen pressure of 44 mbar in 1200 ml ethanol using 10 g W2 Raney nickel. After taking up 4.4 l hydrogen the catalyst was removed by suction filtration and it was rewashed several times with tetrahydrofuran. The evaporated filtrates yielded 12.2 g (70%) VII after triturating with ether, melting point 153° C. (decomp.). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:[Br-].C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1;m1_m2_m3:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m2_m3:O, and Products are 0:S(=O)(=O)([O-])C1=CC=C(C)C=C1.C1(=CC=CC=C1)[S+](C1=CC=CC=C1)C1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of triphenylsulfonium bromide (6.87 g, 20.0 mmol) and p-toluenesulfonic acid (3.80 g, 20.0 mmol) in water (100 ml) was heated at a gentle reflux for 15 hours under nitrogen. After cooling to room temperature, the clear solution was extracted with dichloromethane (4×75 ml). The combined organic extracts were washed with water until neutral (4×75 ml) and dried (MgSO4 ). The solvent was removed under reduced pressure and the residue dried by heating at 80° C. in vacuo for 36 hours to give a crude onium salt as a off-white solid (6.35 g). Recrystallization from acetone-ethyl acetate gave triphenylsulfonium rosylate as a white crystalline solid (5.72 g, 66%). |
Here is a chemical reaction formula: Reactants are:m2:C1(CCCCC1)=O;m3:O;m1_m4:COC1=C(N)C(=CC(=C1)C)OC, Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:C1(CCCCC1)=NC1=C(C=C(C=C1OC)C)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4.2 g of 2,6-dimethoxy-4-methylaniline are dissolved in 50 ml of toluene, 2.45 g of cyclohexanone are then added and the reaction mixture is heated at reflux for 18 hours. The water which is formed is removed as it is formed in the reaction mixture using a Dean and Stark apparatus. The toluene is evaporated and the oily N-cyclohexylidene-2,6-dimethoxy-4-methylaniline residue obtained is used without addition of purification in the following stage. |
Here is a chemical reaction formula: Reactants are:m3:C12C(C3CC(CC(C1)C3)C2)=O;m2:C(=O)O;m1_m4:COC1=C(N)C(=CC(=C1)C)OC, Reagents are:m5:C1(=CC=CC=C1)C;m1_m4:C1(=CC=CC=C1)C, and Products are 0:C12C(C3CC(CC(C1)C3)C2)NC2=C(C=C(C=C2OC)C)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.1 g of 2,6-dimethoxy-4-methylaniline are dissolved in 10 ml of toluene, 0.5 ml of formic acid is then added to this solution and the mixture is heated to gentle reflux, under inert atmosphere, and 0.93 g of 2-adamantanone, dissolved in 10 ml of toluene, is added dropwise at this temperature. The reaction mixture is heated at reflux for 48 hours, is then evaporated to dryness and the residue is taken up in 30 ml of 2N hydrochloric acid. The insoluble white crystals are filtered and discarded. The acidic filtrate is extracted with dichloromethane. The organic extracts are washed with a 5% aqueous sodium bicarbonate solution and then with water and the organic phases are then dried over anhydrous sodium sulphate. Evaporation leaves a colourless residue which is purified by flash chromatography on a column of silica gel, eluent: toluene/ethyl acetate 7/3 (v/v) in order to obtain N-(2-adamantyl)-2,6-dimethoxy-4-methylaniline; M.p.=100° C., Yield 52%. |
Here is a chemical reaction formula: Reactants are:m3:C(CC(C)C)(=O)Cl;m1_m5_m2:COC1=C(N)C(=CC(=C1)C)OC;m1_m5_m2:C(C)N(CC)CC;m4:O, Reagents are:m1_m5_m2:C(C)OCC, and Products are 0:COC1=C(C(=CC(=C1)C)OC)NC(CC(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 8.2 g of 2,6-dimethoxy-4-methylaniline are dissolved in 100 ml of diethyl ether at 0° C. under an inert atmosphere, 5.96 g of triethylamine are added to the reaction mixture and then 6.51 g of isovaleryl chloride are added dropwise, while maintaining the temperature at 0° C. The mixture is left at room temperature for 30 minutes and is then poured into 250 ml of water. The aqueous phase is extracted with ethyl acetate after separation by settling of the ethereal phase. The organic phases are combined and washed with water, then dried over anhydrous sodium sulphate and evaporated to dryness. The white crystals of N-(2,6-dimethoxy-4-methylphenyl)isovaleramide obtained are washed with diisopropyl ether; M.p.=139° C., Yield: 92%. |
Here is a chemical reaction formula: Reactants are:m4:Cl.COC1=C(N)C(=CC(=C1)C)OC;m1_m2_m3:C(=O)(OC(C)(C)C)NCC(=O)O;m1_m2_m3:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C;m1_m2_m3:CN(C=O)C, Reagents are:m5:C(C)(C)OC(C)C;m7:C(C)N(CC)CC;m6:C(C)(=O)OCC, and Products are 0:C(C)(C)(C)OC(=O)NCC(NC1=C(C=C(C=C1OC)C)OC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 6.6 g of N-Boc-glycine and 15.6 g of BOP are successively added to 100 ml of dimethylformamide and then, at 0° C., 14 ml of triethylamine are added dropwise. The mixture is left for 20 minutes at 0° C. and 6.7 g of 2,6-dimethoxy-4-methylaniline hydrochloride are then added portionwise. The reaction mixture is left at room temperature for 15 hours. 400 ml of ethyl acetate are added to the reaction mixture and the organic phase is successively washed with 3×200 ml of water, with a 1N aqueous sodium hydroxide solution and then with water. The organic phase is dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a semi-crystalline residue which is solidified in diisopropyl ether to provide N-tert-butyloxycarbonyl-[(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine, in the form of white crystals; M.p.=146° C.; Yield: 96%. |
Here is a chemical reaction formula: Reactants are:m5:O;m1_m2_m7:Cl.COC1=C(C(=CC(=C1)C)OC)N(C(=O)CN)CCC(C)C;m1_m2_m7:Cl.COC1=C(C(=CC(=C1)C)OC)N(C(=O)CN)CCC(C)C;m6_m3_m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C;m6_m3_m4:C(C)N(CC)CC;m6_m3_m4:COC(=O)CN1C(=CC2=CC=CC=C12)C(=O)O, Reagents are:m1_m2_m7:CN(C=O)C, and Products are 0:COC(CN1C(=CC2=CC=CC=C12)C(NCC(N(CCC(C)C)C1=C(C=C(C=C1OC)C)OC)=O)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.8 9 of [(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylamine hydrochloride (compound 100) is dissolved in 10 ml of dimethylformamide and 0.58 g of 1-(methoxycarbonylmethyl)-2-indolecarboxylic acid, 1.12 g of BOP and then, dropwise, 0.75 g of triethylamine are successively added to the reaction mixture at room temperature. The reaction mixture is left at room temperature for 20 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are washed with water and then dried over anhydrous sodium sulphate. Evaporation of the solvent leaves a yellow oil which is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain white crystals of methyl{2-[[(2,6-dimethoxy-4-methylphenyl)(isopentyl)carbamoyl]methylcarbamoyl]-1-indolyl}acetate; M.p.=141° C.; Yield: 91%. |
Here is a chemical reaction formula: Reactants are:m7_m3_m4:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C;m7_m3_m4:C(C)N(CC)CC;m1_m2_m6:Cl.C1(CCCCC1)CN(C(=O)CN)C1=C(C=C(C=C1OC)C)OC;m1_m2_m6:Cl.C1(CCCCC1)CN(C(=O)CN)C1=C(C=C(C=C1OC)C)OC;m1_m2_m6:CN(C=O)C;m5:O, Reagents are:m7_m3_m4:C(#N)CCN1C(=CC2=CC=CC=C12)C(=O)O, and Products are 0:C1(CCCCC1)CN(C(=O)CNC(=O)C=1N(C2=CC=CC=C2C1)CCC#N)C1=C(C=C(C=C1OC)C)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.5 g of [(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylamine hydrochloride (compound 113) are dissolved in 10 ml of dimethylformamide and 0.918 g of 1-(2-cyanoethyl)-2-indolecarboxylic acid, 1.95 g of BOP and then, dropwise, 1.28 g of triethylamine are then successively added. The reaction mixture is left at room temperature for 3 hours, is then poured into cold water and the aqueous phase is extracted with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residue is purified by flash chromatography on a column of silica gel, eluent: dichloromethane/methanol 98/2 (v/v) in order to obtain 3-{2-[[(cyclohexylmethyl)(2,6-dimethoxy-4-methylphenyl)carbamoyl]methylcarbamoyl]-1-indolyl}propionitrile in the form of a pasty foam; Yield: 91%. |
Here is a chemical reaction formula: Reactants are:m4:C(C)N1CCOCC1;m1_m2_m3_m7:COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCN)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC;m1_m2_m3_m7:F[P-](F)(F)(F)(F)F.N1(N=NC2=C1C=CC=C2)O[P+](N(C)C)(N(C)C)N(C)C;m1_m2_m3_m7:C(C=CC1=CC=CC=C1)(=O)O, Reagents are:m5:C(C)(=O)OCC;m6:O;m1_m2_m3_m7:CN(C=O)C, and Products are 0:COC1=C(C(=CC(=C1)C)OC)CCCCCNC(=O)[C@@H](CCCCNC(C=CC1=CC=CC=C1)=O)NC(=O)C=1N(C2=CC=CC=C2C1)CC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.87 g of methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-aminopentyl}carbamoyl]indol-1-yl}acetate, 0.645 g of BOP and 0.23 g of cinnamic acid are successively added to 30 ml of dimethylformamide. After cooling to -5° C., 0.26 g of N-ethylmorpholine is added under an inert atmosphere and the reaction mixture is maintained at 0° C. for 2 hours and is then left at room temperature for 18 hours. The reaction mixture is poured into a large volume of water and extraction is carried out with ethyl acetate. The organic extracts are dried over anhydrous sodium sulphate and evaporated to dryness. The residual oil is purified by flash chromatography on silica gel, eluent: CH2Cl2 /CH3OH 97/3 (v/v) in order to obtain methyl (R)-{2-[N-{1-[(2,6-dimethoxy-4-methylphenyl)pentylcarbamoyl]-5-(cinnamoylamino)pentyl}carbamoyl]indol-1-yl}acetate in the form of an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1(=CC(=CC=C1)C(=O)Cl)C;m1_m2:ClC1=CC=C(C=C1)Cl;m4:Cl;m3:[Cl-].[Al+3].[Cl-].[Cl-], Reagents are:m5:CCOCC, and Products are 0:ClC1=C(C(=O)C2=CC(=CC=C2)C)C=C(C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of m-toluoyl chloride (22 g, 0.17 mol) and 1,4-dichlorobenzene (120 g, 0.82 mol) was heated to 100° C. in a flask. Aluminum chloride (60 g, 0.45 mol) was added in one portion. Hydrogen chloride started to evolve from the solution. The mixture was heated to 170° C. in 30 min. and stirred at this temperature for 3 hours. The resulting brownish solution was cooled to about 80° C. and poured onto ice. Ether (50 ml) was added. The organic layer was separated and distilled under vacuum after the removal of ether. The residue from distillation was recrystallized twice from hexane to give 20 g of white crystals (53%). |
Here is a chemical reaction formula: Reactants are:m4:Cl;m1_m2_m3_m6:[N+](=O)([O-])C1=C(C=CC(=C1)[N+](=O)[O-])O;m1_m2_m3_m6:C(CCCCCCCCCCCCCCCCC)Br;m1_m2_m3_m6:C([O-])([O-])=O.[Na+].[Na+], Reagents are:m1_m2_m3_m6:CN(C=O)C;m5:O, and Products are 0:C(CCCCCCCCCCCCCCCCC)OC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2,4-dinitrophenol (85 wt %, 6.72 g, 31 mmol), octadecyl bromide (20.7 g, 62 mmol), sodium carbonate (6.57 g, 62 mmol) and dimethylformamide (31 mL) was heated to 100° C. under a nitrogen atmosphere for 22 h. The cooled mixture was diluted with water (200 mL), acidified with 10N hydrochloric acid (50 mL) and extracted with ether. The extracts were washed with water and brine, and dried over magnesium sulfate. The solvent was removed and the solid recrystallized to give 1-octadecyloxy-2,4-dinitrobenzene (10.7 g, 79%): mp 63.5°-64.0° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-];m1_m2_m3_m4:C([O-])([O-])=O.[Na+].[Na+];m1_m2_m3_m4:C(CCCCCCCCCCCCCCCCC)NCCCCCCCCCCCCCCCCCC;m1_m2_m3_m4:CN(C=O)C, Reagents are:m5:O, and Products are 0:C(CCCCCCCCCCCCCCCCC)N(C1=C(C=C(C=C1)[N+](=O)[O-])[N+](=O)[O-])CCCCCCCCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-chloro-2,4-dinitrobenzene (Aldrich, 2.02 g, 10 mmol), sodium carbonate (1.27 g, 12 mmol), dioctadecylamine (Pfaltz & Bauer, 6.26 g, 12 mmol) and dry dimethylformamide (10 mL) was heated to 80°-90° C. under a nitrogen atmosphere for 1 h. The cooled mixture was diluted with water and extracted with ether. The extracts were washed with water and dried over magnesium sulfate. The solvent was removed and the solid recrystallized to give N,N-dioctadecyl-2,4-dinitrobenzenamine (6.0 g, 87%): mp 55.5°-57.5° C. |
Here is a chemical reaction formula: Reactants are:m3_m4_m0:C(C)(=O)OCC;m1_m2_m5:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O;m1_m2_m5:CC=1NC(=C(CC1C(=O)OCC)C(=O)OCC)C, Reagents are:m3_m4_m0:C1(=CC=CC=C1)C;m1_m2_m5:C1(=CC=CC=C1)C, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)CC1C(NC(S1)=S)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 13.98 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-thiazolidinone, 13.17 g of diethyl 2,6-dimethyl-1,4-dihydro-3,5-pyridinedicarboxylate and 600 ml of toluene were stirred to effect solution. Forty grams of silica gel 60 (finer than 230 mesh) previously dried in vacuo at 50° C. for 7 hours were added to the reaction. The reaction was heated at reflux for 18 hours and filtered hot. The filtrate was evaporated to dryness. The residue was dissolved in 500 ml of ethyl acetate, washed 5 times each with 400 ml of 1N hydrochloric acid, dried over sodium sulfate, filtered, and evaporated in vacuo to provide a yellow solid. Chromatography over silica gel eluting with 2.5% ethyl acetate in toluene provided 8.0 g of the desired title product, m.p. 178°-179° C. |
Here is a chemical reaction formula: Reactants are:m0_m1_m2:C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C;m0_m1_m2:CN1C(SCC1=O)=S, Reagents are:, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared in 76% yield from 3,5-di-tert-butyl-4-hydroxybenzaldehyde and N-methylrhodanine following the procedure of Example 1, m.p. >230° C. |
Here is a chemical reaction formula: Reactants are:m0_m1:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)C)=O;m2_m3_m5:C(CCC)[SnH](CCCC)CCCC;m2_m3_m5:N(=NC(C#N)(C)C)C(C#N)(C)C;m4:O, Reagents are:m2_m3_m5:C1(=CC=CC=C1)C, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared in 71% yield from 10.31 g of the thione of Example 9 upon heating with 38.15 ml of tri-n-butyl tin hydride and 1.16 g of azobisisobutyronitrile (AIBN) in 142 ml of toluene at reflux temperature for one hour. The product was isolated by adding water to the cooled reaction mixture, separating the layers, washing the organic layer with 1N hydrochloric acid and a saturated sodium chloride solution, drying over magnesium sulfate, concentrating in vacuo, and purifying the residue by chromatography over silica gel eluting with a 10-50% hexane in ethyl acetate gradient. The purified product had a melting point of 142°-144° C. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O;m1_m5_m2:[H-].[Na+];m4:Cl;m3:C(C)I, Reagents are:m1_m5_m2:O1CCCC1;m6_m7:C(C)OCC;m6_m7:O, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 9.58 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-4-thiazolidinone in 150 ml of tetrahydrofuran were added 1.20 g of a 60% dispersion of sodium hydride in mineral oil. After gas evolution ceased, 2.4 ml of ethyl iodide were added and the reaction mixture was stirred for two days under an argon atmosphere. The mixture was heated at reflux for six hours, cooled, diluted with diethyl ether and water, and adjusted to pH 3 with 1N hydrochloric acid. The layers were separated, and the organic layer was washed with a saturated sodium bicarbonate solution followed by a saturated sodium chloride solution. Concentration of the dried organic solution and chromatography of the resulting residue over silica gel eluting with a 10-30% ethyl acetate in hexane gradient provided 3.65 g of the desired title product, m.p. 169°-172.5° C. |
Here is a chemical reaction formula: Reactants are:m3_m4:C(O)CN;m1_m2:C(=S)=S;m1_m2:C(C)OCC, Reagents are:m3_m4:C(C)O, and Products are 0:OCCN1C(SCC1=O)=S, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sixty milliliters of carbon disulfide were added to 200 ml of diethyl ether. The solution was chilled to -5° C. and slowly added to a solution of 138 ml of ethanolamine in 250 ml of ethanol. After holding the mixture at ambient temperature for 16 hours, the resulting top layer was decanted and the residual oil washed twice with 50 ml of diethyl ether. To the oil was added a solution of 71 g of chloroacetic acid in 150 ml of 5N sodium hydroxide at 0° C. The cooling bath was removed and the reaction was allowed to stand for 75 minutes. The mixture was poured into 400 ml of 6N hydrochloric acid and the resulting mixture heated to 91° C. for 20 minutes. The heat was removed, and the solution allowed to stand for 5 hours at ambient temperature. An oily organic layer was separated from the aqueous layer and the aqueous layer extracted twice with 250 ml of ethyl acetate. The organic layers were combined, washed twice with a saturated sodium chloride solution, dried and concentrated in vacuo to provide 113.4 g of the desired subtitled intermediate, which was used without further purification. |
Here is a chemical reaction formula: Reactants are:m1_m4:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(C(S1)=S)CCOC(C)=O)=O;m2_m3:C(CCC)[SnH](CCCC)CCCC;m2_m3:CC(C)(C#N)N=NC(C)(C)C#N, Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCOC(C)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 82.2 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-[2-(acetyloxy) ethyl]-2-thioxo-4-thiazolidinone in 950 ml of toluene was heated to 65° C. Tri-n-butyl tin hydride (219.7 g) and AIBN (4.65 g) were added and the solution heated at reflux temperature for an additional 10 minutes. After cooling, the mixture was washed with 1.25l of 1N hydrochloric acid followed by 500 ml of a saturated sodium chloride solution. The organic layer was stripped and allowed to stand overnight, during which time a precipitate separated. The liquid portion was decanted off, and the resulting residue was purified by chromatography over silica gel, eluting with a gradient of 25-50% of ethyl acetate in hexane. The appropriate fractions were combined and concentrated in vacuo to provide 45.7 g of the desired titled compound, m.p.=152°-155° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCOC(C)=O)=O;m1_m3_m2:[OH-].[NH4+], Reagents are:m1_m3_m2:C(C)#N, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CCO)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 85.2 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-3-[2-(acetyloxy)ethyl]-4-thiazolidinone from Example 26 in 1.5 l of acetonitrile was treated with 1 liter of concentrated ammonium hydroxide. The reaction mixture was allowed to stand for approximately 90 hours at room temperature. The solution was concentrated in vacuo and 500 ml of ethyl acetate were added, with the pH adjusted to 3.0 with concentrated hydrochloric acid. The layers were separated and the aqueous layer extracted with 250 ml of ethyl acetate. The combined organic layers were washed with 250 ml of a saturated sodium chloride solution and concentrated in vacuo. The residue was crystallized from 95 ml of hexane and 70 ml of ethyl acetate to provide 35.68 g of the desired subtitled intermediate, m.p. 131°-135° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NCS1)=O;m1_m2_m3_m4:BrCC#N;m1_m2_m3_m4:[H-].[Na+], Reagents are:m1_m2_m3_m4:O1CCCC1, and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N(CS1)CC#N)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 7.03 g of 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-thiazolidinone and 2.64 g of bromoacetonitrile were reacted in the presence of 0.97 g of 60% sodium hydride in mineral oil and 330 ml of tetrahydrofuran. Work-up of the reaction mixture provided 3.21 g of the desired title product, m.p. 186°-188° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC(C)(C)C1=C(C(=CC=C1)C)O;m1_m2_m3:C1N2CN3CN1CN(C2)C3;m1_m2_m3:FC(C(=O)O)(F)F, Reagents are:, and Products are 0:CC(C)(C)C=1C=C(C=O)C=C(C1O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 76.65 g of 2-(1,1-dimethylethyl)-6-methylphenol (Aldrich), 65.42 g of hexamethylenetetramine and 700 ml of trifluoroacetic acid were stirred at reflux temperature for about 24 hours, then allowed to cool and evaporated. The residue from the evaporation was taken up in 1500 ml of water and 1000 ml of chloroform and neutralized to pH 7 with solid sodium carbonate. The resultant layers were separated and the aqueous layer was washed with chloroform. The organic layer was dried over sodium sulfate overnight, after which it was again washed with a volume of chloroform and evaporated. The resultant residue was then taken up in 375 ml of toluene, heated on a steam bath and then allowed to cool to room temperature overnight. Subsequent workup gave 28.3 g of the desired subtitled intermediate. |
Here is a chemical reaction formula: Reactants are:m1:CN(C1=CC=CC=C1)C=O;m3:C(C)(C)(C)C1=C(C=CC=C1)O;m2:P(=O)(Cl)(Cl)Cl, Reagents are:, and Products are 0:CC(C)(C)C=1C=C(C=O)C=CC1O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into 101.5 g of N-methylformanilide was added dropwise with cooling 107 g of phosphoryl chloride over a period of 15 minutes. The mixture was allowed to warm to room temperature and stirred for 70 minutes. 67.5 g of ortho-t-butylphenol was added and stirred for about 45 minutes after which the mixture was heated to about 50°-60° C. and allowed to stir for 4.5 hours. The reaction mixture was poured into a volume of crushed ice and extracted with chloroform. The aqueous layer was separated and washed again with chloroform. The chloroform layers were combined and extracted with 2000 ml of a 5% potassium hydroxide solution. The aqueous potassium hydroxide layer was separated and added to 1000 ml of chloroform. The pH of the resulting two-phase mixture was adjusted to 3 with concentrated hydrochloric acid with stirring. The resultant layers were separated and the aqueous layer was again extracted with chloroform and dried over sodium sulfate overnight to give 18.1 g of the desired subtitled intermediate. |
Here is a chemical reaction formula: Reactants are:m1:CC(C)(C)C=1C=C(C=C(C1O)C)C=C1C(NCS1)=O, Reagents are:m2:O1CCCC1;m3:[Pd], and Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C)CC1C(NCS1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 0.28 g of the compound of Example 61 in 30 ml of tetrahydrofuran was hydrogenated at 60 pounds per square inch in the presence of 1.12 g of 5% palladium on carbon overnight at 60° C. The reaction mixture was filtered and evaporated to dryness. The resulting residue was dissolved in 3.5 ml of a 1:1.5 ethyl acetate/hexane solution and loaded onto a silica gel chromatography column. Elution with 40% ethyl acetate in hexane produced fractions which, upon evaporation to dryness, provided 0.05 g of title compound. m.p. 64°-68° C. |
Here is a chemical reaction formula: Reactants are:m5:C(C)(=O)OCC;m2:[Mg];m3:[Mg];m1_m6:CC(C)(C)C=1C=C(C=CC1O)C=C1C(NCS1)=O;m4:[Mg], Reagents are:m1_m6:CO, and Products are 0:CC(C)(C)C=1C=C(C=CC1O)CC1C(NCS1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A portion of the title compound from Example 77 (395.1 mg; 1.5 mmol) was dissolved in 9 ml of methanol. Magnesium (72.9 mg; 3.0 mmol) was then added to the solution and the resulting reaction mixture was stirred at room temperature for 3 hours. After 3 hours, most of the magnesium which had been added originally appeared to be gone so an additional 182.3 mg (7.5 mmol) of magnesium were added. Stirring of the reaction solution at room temperature continued overnight. By the next morning a yellow precipitate had formed. This precipitate was dissolved by adding the methanolic reaction solution to an ethyl acetate/1N hydrochloric acid mixture. The organic layer from the resulting two-phase mixture was isolated and then dried over sodium sulfate. The volatile components of the organic layer were removed and the resulting residue was chased with methylene chloride. The residue was then dissolved in 25 ml of methylene chloride and the resulting solution was chromatographed on a silica gel chromatography column using a 5-20% isopropyl alcohol in hexanes gradient. Those fractions identified as containing essentially pure product were evaporated to provide 0.29 g of title compound. m.p. 65°-70° C. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=C(C=CC=C1)CC#N;m1:ClCCN1CCCCC1, Reagents are:, and Products are 0:ClC1=C(C=CC=C1)C(C#N)CCN1CCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The present invention relates to a novel process for the preparation of N-heterocyclealkanamide derivatives having the following formula: ##STR1## which comprises reacting 1-(2-chloroethyl)piperidine with 2-chlorobenzeneacetonitrile to give (±)-α-(2-chlorophenyl)-1-piperidinebutanenitrile; alkylating the piperidenebutanenitrile to give (±)-α-(2-chlorophenyl)-α-(2,2-dimethoxyethyl)piperidine-1-butanenitrile; hydrolyzing the resulting alkylated piperidinebutanenitrile to give (±)-α-(2-chlorophenyl)-α-(2-oxoethyl)piperidine-1-butanenitrile; reacting the resulting piperidinebutanenitrile with isopropylamine to form (±)-α-(2-chlorophenyl)-α-[2-[(1-methylethyl)imino]ethyl]piperidine-1-butanenitrile; reducing the resulting imine to form (±)-α-(2-chlorophenyl)-α-[2-[(1-methylethyl)amino]ethyl]-piperidine-1-butanenitrile; acetylating the resulting amine to form (±)-N-[3-(2-chlorophenyl)-3-cyano-5-(1-piperidinyl)pentyl]-N-(1-methylethyl)acetamide; hydrolyzing the resulting acetylated amino substituted piperidine butanenitrile to form (±)-α-[2-[acetyl(1-methylethyl)amino]ethyl]-α-(2-chlorophenyl)-1-piperidinebutanamide; and isolating the resulting piperidinebutanamide. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:FC1=C(C(=O)O)C=C(C(=C1F)F)F;m1_m2_m3:S(=O)(Cl)Cl, Reagents are:m1_m2_m3:CN(C=O)C, and Products are 0:FC1=C(C(=O)Cl)C=C(C(=C1F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 200 g of 2,3,4,5-tetrafluorobenzoic acid, 225 ml of thionyl chloride and 5 ml of N,N-dimethylformamide, prepared at 20° C., is heated at reflux for 3 hours. After cooling at 40° C., the thionyl chloride in excess is evaporated off under vacuum. The residue is taken up with toluene and the solution is concentrated again at 40° C. under vacuum. Thus 219 g of raw 2,3,4,5-tetrafluorobenzoyl chloride are obtained as a yellowish oil. A mixture of 1200 ml of toluene, 220 g of diethyl malonate and 153 g of magnesium ethylate, prepared at 20° C., is heated one hour at reflux, then it is cooled to 5° C. and the acid chloride above obtained is added thereto, by keeping the temperature below 10° C. After a 30-minutes stirring, the mixture is made acid with concentrated hydrochloric acid and the two phases are separated. The organic phase is diluted with water, made acid with sulfuric acid to pH 1.0 and heated at reflux for 7 hours, namely until the reaction is over. The mixture is cooled, the aqueous phase is separated and the organic one is taken up with water and made basic with sodium hydroxide to a very basic pH value. The aqueous phase is separated and the organic one is again extracted with water. The combined aqueous phases are made acid with concentrated hyarochloric acid to pH 1 and extracted twice with toluene. The toluene phase is concentrated under vacuum, the residue is taken up with 1250 ml of acetonitrile. To this mixture, at first 80 g of sodium bicarbonate and then 110 ml of N-methylpiperazine are added and the reaction mixture is heated 3 hours at reflux. By dilution with water the desired product precipitates and it is then filtered and washed with water. The wet product thus obtained is suspended in toluene and the suspension is evaporated by distillation until the solution becomes anhydrous. This solution contains 0.89 mole of ethyl 2,3,5-trifluoro-4-(4-methylpiperazin-1-yl)benzoylacetate and is directly used for the subsequent step (b). |
Here is a chemical reaction formula: Reactants are:m2_m3:ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C#N)O;m2_m3:S(O)(O)(=O)=O, Reagents are:, and Products are 0:ClC1=C2C(=CC=NC2=CC(=C1)Cl)O;0:ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C#N)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5,7-Dichloro-3-cyano-4-hydroxyquinoline (7.0 g; 0.0293 mole) and 104 g of 62.5% sulfuric acid were charged in a 300 ml four-necked flask equipped with stirrer, thermometer and reflux condenser, and the mixture was heated up to a boiling point (144°-146° C.) during one hour and subjected to a reaction at the same temperature for 15 hours. When the reaction product was analyzed by liquid chromatography, 5,7-dichloro-4-hydroxyquinoline was produced in 99% yield (where the starting 5,7-dichloro-3-cyano-4-hydroxyquinoline disappeared while an intermediate, 5,7-dichloro-3-carboxy-4-hydroxyquinoline, was produced in not more than 0.2% yield). |
Here is a chemical reaction formula: Reactants are:m4:ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)OCC)O;m2_m3:ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)OCC)O;m2_m3:S(O)(O)(=O)=O, Reagents are:m5:C(C)O, and Products are 0:ClC1=C2C(=C(C=NC2=CC(=C1)Cl)C(=O)O)O;0:ClC1=C2C(=CC=NC2=CC(=C1)Cl)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5,7-Dichloro-3-ethoxycarbonyl-4-hydroxyquinoline (114.4 g; 0.4 mole) and 343.2 g of 70% sulfuric acid were charged in a 1,000 ml four-necked flask equipped with stirrer, thermometer and distilling tube and the mixture was heated at 150° C. with stirring. Reaction was continued by heating up to 165° C. during three hours together with evaporation of the by-produced ethanol outside the reaction system. The reaction product was analyzed by liquid chromatography whereupon and it was found that the starting 5,7-dichloro-3-ethoxycarbonyl-4-hydroxy-quinoline disappeared and that 5,7-dichloro-3-carboxy-4-hydroxyquinoline in 22% yield and 5,7-dichloro-4-hydroxyquinoline in 78% yield were produced. |
Here is a chemical reaction formula: Reactants are:m3:BrCC(=O)Br;m1:C1(CCCCCC1)N;m2:C(C)(C)N(CC)C(C)C, Reagents are:m5:O;m4:C(Cl)Cl, and Products are 0:BrCC(=O)NC1CCCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a -20° C. solution of cycloheptylamine (6.37 mL, 50.0 mmol) and diisopropylethylamine (9.58 mL, 55.0 mmol) in methylene chloride (250 mL) was slowly added bromoacetyl bromide (4.78 mL, 55.0 mmol). The reaction mixture was warmed to room temperature over 20 minutes and stirred for an addition 30 minutes. The reaction mixture was diluted with water (100 mL) and stirred for an additional 30 minutes. The organic layer was separated, washed with water (3×100 mL), dried over magnesium sulfate and concentrated in vacuo to afford a beige solid (10.5 g). The crude material was further purified by silica gel flash column chromatography using hexane-ethyl acetate (1:1) as the eluent to give the purified title compound as a whim solid (9.77 g, 83%). |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:Cl.C(C1=CC=CC=C1)ON;m1_m4_m2_m3:BrCC(=O)Br;m1_m4_m2_m3:C(C)(C)N(CC)C(C)C, Reagents are:m5_m6:C(C)(=O)OCC;m5_m6:O;m1_m4_m2_m3:C1CCOC1, and Products are 0:BrCC(=O)NOCC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 0° C. solution of O-benzylhydroxylamine hydrochloride (1.6 g, 10 mmol) in THF (40 mL) was added bromoacetyl bromide (871 μL, 10 mmol) and diisopropylethylamine (3.5 mL, 20 mmol). The reaction mixture was warmed to room temperature overnight and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel flash column chromatography with ethyl acetate-hexane to give 1.27 g (52%) of the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3:C(C)(C)C1=C(C=CC=C1)S;m1_m2_m5_m3:CN(C)CCN(C)C;m1_m2_m5_m3:[Li]CCCC;m4:C(=O)=O, Reagents are:m1_m2_m5_m3:C1CCCCC1, and Products are 0:SC1=C(C(=O)O)C=CC=C1C(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1.0 mmol 2-isopropylthiophenol and 2.2 mmol TMEDA in 2 mL cyclohexane was added 2.2 mmol n-BuLi. Then after stirring 24 h it was added to solid CO2 and stirred for 16 h when extraction and chromatography provided 2-mercapto-3-isopropylbenzoic acid. The methyl ester of this was treated as in example 3 to provide the title compound. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:Cl.COC(CNCC(=O)OC)=O;m1_m2_m3_m4:C(C)(C)N(C(C)C)CC;m1_m2_m3_m4:BrCCCBr, Reagents are:m1_m2_m3_m4:C1(=CC=CC=C1)C, and Products are 0:BrCCCN(CC(=O)OC)CC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1 mmol iminodiacetic acid dimethylester hydrochloride salt, 5 mmol N,N-diisopropyl-ethylamine and 3 mmol 1,3-dibromopropane in 2 mL toluene was stirred at 90° C. for 16 h and then chromatographed to provide the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3:Cl.CN;m1_m2:IC=1C=C(C(=O)O)C=CC1C;m1_m2:S(=O)(=O)(C1=CC=C(C)C=C1)Cl, Reagents are:, and Products are 0:CNC(=O)C1=CC(=C(C=C1)C)I, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.0 mmol of 3-iodo-4-methylbenzoic acid, 1.2 mmol of TsCl, and 25 mmol of Py was stirred for 3 h and then 5 mmol of methylamine hydrochloride was added and stirring continued for 5 h. Chromatography provided N-methyl-(3-iodo-4-methylphenyl)carboxamide. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:Cl.COC([C@@H](N)CC1=CC=CC=C1)=O;m1_m2_m5:C(C)N(CC)CC;m3_m4:C(=O)O;m3_m4:C(C)(=O)OC(C)=O, Reagents are:m1_m2_m5:CN(C)C=O, and Products are 0:COC([C@@H](NC=O)CC1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 1 mmol of phenylalanine methyl ester hydrochloride and 2 mmol of triethylamine in 1 mL of DMF at 0 ° C. was added 2 mL of formic acid and 0.7 mL of acetic anhydride. After stirring for 16 h at rt, extractive isolation provided N-formylphenylalanine methyl ester. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m5:C1(CCCCCO1)=O;m1_m4_m2_m5:[Li+].CC(C)[N-]C(C)C;m3_m6:C(C1=CC=CC=C1)Br, Reagents are:m1_m4_m2_m5:C1CCOC1;m1_m4_m2_m5:C1CCOC1;m3_m6:CN1CCCN(C1=O)C, and Products are 0:C(C1=CC=CC=C1)C1C(=O)OCCCC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1 mmol of caprolactone in 0.5 mL THF was added to a solution of LDA in 0.5 mL THF at -78° C. and this stirred for 2 h. Then a solution of 1.1 mmol of a benzylbromide in 0.14 mL DMPU was added to the above mixture and after stirring for 1 h at -15° C., the 2-benzylcaprolactone was isolated by extraction and chromatography. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:BrC=1C=C(C(=O)OCC)C=CC1C;m1_m2_m3_m4:C1CC(=O)N(C1=O)Br;m1_m2_m3_m4:C(C1=CC=CC=C1)(=O)OOC(C1=CC=CC=C1)=O, Reagents are:m1_m2_m3_m4:C(Cl)(Cl)(Cl)Cl, and Products are 0:BrC=1C=C(C(=O)OCC)C=CC1CBr, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of ethyl 3-bromo-4-methylbenzoate, 1.0 mmol NBS, and 0.02 mmol benzoyl peroxide in 5 mL CCl4 was refluxed for 4 h and then processed by filtration and chromatography to provide ethyl 3-bromo-4-bromomethylbenzoate as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:BrC=1C=C(C=CC1)CC(=O)OCC;m1_m2_m4_m3:C(=C)[Sn](CCCC)(CCCC)CCCC, Reagents are:m1_m2_m4_m3:CN(C)C=O;m1_m2_m4_m3: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:C(=C)C=1C=C(C=CC1)CC(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of ethyl 3-bromophenylacetate, 1.5 mmol of vinyltributyltin, and 0.1 mmol of Pd(PPh3)4 in 4 mL DMF was stirred and heated at 90° C. for 1-16 h. Chromatography provided ethyl 3-vinylphenylacetate. |
Here is a chemical reaction formula: Reactants are:m3_m5:II;m1_m2_m4:IC=1C=C(C(=O)O)C=CC1C;m1_m2_m4:[BH4-].[Na+], Reagents are:m3_m5:C1CCOC1;m1_m2_m4:C1CCOC1, and Products are 0:IC=1C=C(CO)C=CC1C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of 3-iodo-4-methylbenzoic acid and 1.2 mmol of NaBH4 in 4 mL of anhydrous THF was stirred for 30 min and then 0.5 mmol of iodine in 2.0 mL of THF at 5° C. was added. After stirring for 2 h the mixture was processed by extraction to provide 3-iodo-4-methylbenzyl alcohol. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:IC=1C=C(CO)C=CC1C, Reagents are:m1_m3_m2:C(Cl)Cl;m1_m3_m2:O=[Mn]=O, and Products are 0:IC=1C=C(C=O)C=CC1C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of this alcohol and 5.0 mmol of MnO2 in 5 mL of CH2Cl2 was stirred for 16 h at rt. Chromatography provided 3-iodo-4-methylbenzaldehyde. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2_m4:IC=1C=C(C=O)C=CC1C;m1_m3_m2_m4:[Li]CCCC, Reagents are:m1_m3_m2_m4:[Br-].C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1;m1_m3_m2_m4:C1CCOC1, and Products are 0:IC=1C=C(C=C)C=CC1C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: This aldehyde (1 mmol)was added to a premixed solution of 1.5 mmol of methyl triphenylphosphonium bromide and 1.2 mmol of n-BuLi in 5 mL of THF at 0° C. and this mixture was stirred for 3-6 h at rt and then processed by extraction and chromatography to give 3-iodo-4-methylstyrene. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:BrC=1C=C(C=O)C=CC1F;m1_m2_m3_m4_m5:CN(C)C=O;m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:CO, Reagents are:m1_m2_m3_m4_m5: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(C=O)C=CC(=C1C(=O)OC)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of 3-bromo-4-fluorobenzaldehyde, 4 mL of DMF, 0.2 mL of triethylamine, 0.4 mL of MeOH and 0.05 mmol of Pd(PPh3)4 was heated at 90° C. at 40 psi under CO atmosphere for 16 h. Extraction and chromatography provided methyl 3-carbomethoxy-4-fluorobenzaldehyde. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:OC1=CC=C(C(=O)OC)C=C1;m1_m2_m3_m4:C(C=C)Br;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], Reagents are:m1_m2_m3_m4:CC(=O)C, and Products are 0:C(C=C)OC1=CC=C(C(=O)OC)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.0 mmol of methyl 4-hydroxybenzoate, 2.0 mmol of allyl bromide, 5.0 mmol of K2CO3 in 2 mL of acetone was stirred for 16 h. Extraction provided methyl 4-allyloxybenzoate. |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[Na+];m3:C[Si](C)(C)CCOCCl;m2_m5:N1N=NN=C1, Reagents are:m1_m4:CN(C)C=O;m2_m5:CN(C)C=O, and Products are 0:C[Si](C)(C)CCOCC1=NN=NN1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a Suspension of 1.1 mmol NaH in 5 mL DMF at 0° C. was added a solution of 1.0 mmol tetrazole in 2 mL DMF. After 30 min, trimethylsilylethoxymethylchloride was added and the mixture stirred for 16 h. Extraction and chromatography provided trimethylsilylethoxymethyltetrazole as an oil. |
Here is a chemical reaction formula: Reactants are:m7_m5:[OH-].[Na+];m1_m2_m3_m4_m6:C(#N)CCCNC(=O)C1=CC(=C(C=C1)C)Br;m1_m2_m3_m4_m6:[Si](C)(C)(C)N=[N+]=[N-];m1_m2_m3_m4_m6:C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3;m1_m2_m3_m4_m6:CCOC(=O)/N=N/C(=O)OCC, Reagents are:m7_m5:C1CCOC1;m1_m2_m3_m4_m6:C1CCOC1, and Products are 0:BrC=1C=C(C=CC1C)C1=NN=NN1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 1.0 mmol of this amide, 4.0 mmol of TMSN3, 4.0 mmol of PPh3, and 4.0 mmol of DEAD in 4 mL of THF at 0° C. was stirred 24 h and then concentrated. The residue was mixed with 5 mL of THF and 12.0 mmol of 1N NaOH. After stirring for 24 h and processing by extraction, 5-(3'-bromo-4'-methylphenyl)tetrazole was obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:Cl.C(C)OC(CN)=O;m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:C1(CCCCC1)N=C=NC1CCCCC1;m1_m2_m3_m4_m5:ON1C(CCC1=O)=O;m1_m2_m3_m4_m5:CN(C)C=O, Reagents are:, and Products are 0:C(C)OC(CNC(CCCN1C=NC2=C1N=CNCC2O)=O)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1 mmol of 3-(3'-carbobenzyloxypropyl)coformycin aglycone and10 mg of 10% Pd/C in 4 mL of methanol was subjected to hydrogenation. After filtration and removal of the solvent, 3-(3'-carboxypropyl)coformycin aglycone was obtained. This product, 2 mmol glycine ethyl ester hydrochloride, 2 mmol triethylamine, 2 mmol dicyclohexylcarbodiimide and 2 mmol N-hydroxysuccinimide in 10 mL DMF were stirred 16 h and filtered. Chromatography provided N-(4-(3,6,7,8-tetrahydro-imidazo[4,5-d]-[1,3]diazepin-8-ol-3-yl)butyryl)glycine ethyl ester. |
Here is a chemical reaction formula: Reactants are:m5:C(Cl)(Cl)Cl;m1:NC1=CC=C(OC(C(=O)O)(C)C)C=C1;m2_m3_m4:[OH-].[Na+];m2_m3_m4:C(C)(=O)NC1=CC=C(C=C1)O;m2_m3_m4:CC(=O)C, Reagents are:, and Products are 0:N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: FIG. 2A illustrates a reaction scheme for preparing 2-(4-aminophenoxy)-2-methyl propionic acid, a compound that is useful as a precursor in the preparation of Group I compounds. In accordance with the scheme of FIG. 2A, 8 grams (g) (0.2 mol) of pulverized sodium hydroxide is added to a suspension of 5.28 g (0.035 mol) of p-acetamidophenol in 23 ml (0.4 mol) of acetone. The reaction mixture is stirred at room temperature for 1/2 hour. Subsequently, 3.58 g (0.03 mol) of chloroform is added dropwise over the course of 30 minutes. The reaction mixture is stirred overnight at room temperature and acetone is removed under vacuum. The residue is dissolved in water (10 ml), followed by acidification with 37% hydrochloric acid (HCl) to produce a pale yellow precipitate of 2-(4-acetaminophenoxy)-2-methyl propionic acid (5 g, 60% yield), crystallized from methanol, mp 69°-71° C. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)O;m1_m3:N(C(=O)C)C1=CC=C(OC(C(=O)O)(C)C)C=C1, Reagents are:m1_m3:[OH-].[K+], and Products are 0:NC1=CC=C(OC(C(=O)O)(C)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.18 g (0.005 mol) of the 2-(4-acetaminophenoxy)-2-methyl propionic acid is boiled in 10% KOH (60 ml) for 1/2 hour. The solution is then cooled and acidified with acetic acid to yield 0.6 g (62% yield) of 2-(4-aminophenoxy)-2-methyl propionic acid as a yellowish white powder, mp 214°-16° C. |
Here is a chemical reaction formula: Reactants are:m3_m4:C(C(C)C)=O;m3_m4:C(Cl)(Cl)Cl;m1_m5_m2:CC=1C=C(C=C(C1)C)NC(CC1=CC=C(C=C1)O)=O;m1_m5_m2:[OH-].[Na+];m1_m5_m2:C1CCOC1, Reagents are:, and Products are 0:CC(C(C(=O)O)OC1=CC=C(C=C1)CC(=O)NC1=CC(=CC(=C1)C)C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. 5.45 ml (60 mmol) of isobutyraldehyde and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirring continued overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% NaHCO3 solution. The aqueous layer on acidification yields the product 3-methyl-2-[4-((((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]butanoic acid (C21H25NO4) (yield 1 gm, 23.5%) mp (uncorrected) 96°-100° C. |
Here is a chemical reaction formula: Reactants are:m2_m6_m3:CC=1C=C(C=C(C1)C)NC(CC1=CC=C(C=C1)O)=O;m2_m6_m3:[OH-].[Na+];m4_m5:C1(CCCCC1)=O;m4_m5:C(Cl)(Cl)Cl, Reagents are:m2_m6_m3:C1CCOC1, and Products are 0:Cl;0:C1(CCCCC1)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (3.06 gms, 12 mmol) in THF is treated with 2.4 gms (60 mmol) of NaOH at -20° C. Subsequently 5.889 gms (60 mmol) of cyclohexanone and 4.8 ml (60 mmol) of CHCl3 is added dropwise simultaneously at -20° C. and stirred overnight at room temperature. THF is removed under vacuum and the residue is dissolved in water, followed by acidification with 35% HCl. The precipitated solid is extracted into ether and treated with 6% sodium bicarbonate solution. The aqueous layer on acidification with HCl yields the product 1-[4-(((3,5-dimethylphenyl)amino)carbonyl)methyl)phenoxy]cyclohexanecarboxylic acid (C23H27NO4). The product was purified by repeated extraction into ether and NaHCO3. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1C(C1)COCCC1=CC=C(C=C1)O;m1_m2:C(Cl)C1CO1, Reagents are:, and Products are 0:C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: reaction 4-[(2-Cyclopropylmethoxy)-ethyl]-phenol with epichlorohydrin in presence of base to form 1- {4-[2-(Cyclopropylmethoxy)-ethyl]-phenoxy}-2,3-epoxypropane; and |
Here is a chemical reaction formula: Reactants are:m1:C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1;m2:C(C)(C)N, Reagents are:, and Products are 0:CC(C)NCC(COC=1C=CC(=CC1)CCOCC2CC2)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: reacting 1-{4-[2-(Cyclopropylmethoxy)ethyl]phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol. |
Here is a chemical reaction formula: Reactants are:m1_m2:C1C(C1)COCCC1=CC=C(C=C1)O;m1_m2:C(Cl)C1CO1, Reagents are:, and Products are 0:C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: reaction 4-[(2-Cyclopropylmethoxy)-ethyl]-phenol with epichlorohydrin in presence of base to form 1-{4-[2-(Cyclopropylmethoxy)-ethyl]-phenoxy}-2,3-epoxypropane; |
Here is a chemical reaction formula: Reactants are:m1:C1(CC1)COCCC1=CC=C(OCC2CO2)C=C1;m2:C(C)(C)N, Reagents are:, and Products are 0:CC(C)NCC(COC=1C=CC(=CC1)CCOCC2CC2)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: reacting 1-{4-[2-(Cyclopropylmethoxy)ethyl]phenoxy}-2,3-epoxypropane with isopropylamine to produce Betaxolol; and |
Here is a chemical reaction formula: Reactants are:m3:C(C)(=O)OCC.CCCCCC;m1_m4_m2_m5:O=C(CC(=O)OC)CCC=CC;m1_m4_m2_m5:[N+](=O)([O-])C=CC1=CC2=C(OCO2)C=C1, Reagents are:m6:C1CCC2=NCCCN2CC1;m1_m4_m2_m5:C(C)(C)O;m1_m4_m2_m5:C1CCOC1, and Products are 0:C(CCC=CC)(=O)C(C(=O)OC)C(C[N+](=O)[O-])C1=CC2=C(OCO2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of methyl 3-oxo-6-octenoate (502 mg, 2.95 mmol) in 10 mL of isopropanol was added to a solution of 5-(2-nitrovinyl)-1,3-benzodioxole (712 mg, 3.69 mmol) in 10 mL THF, then DBU (22 μL, 0.15 mmol) was added. The resulting reddish solution was stirred at room temperature for 20 minutes. TLC (ethyl acetate-hexane, 1:3) indicated complete consumption of ketoester. The solution was concentrated in vacuo and flash chromatographed on silica gel eluting with 18% ethyl acetate in hexane to produce 879 mg (2.42 mmol, 82%) of the title compound as a mixture of diastereomers in a 1:1 ratio. 1H NMR (CDCl3, 300 MHz) δ 1.55-1.66 (m, 3H), 2.02-2.17 (br m, 1H), 2.20-2.37 (m, 1.5H), 2.49-2.76 (m, 1.5H), 3.57 (s, 1.5H), 3.74 (s, 1.5H), 3.97 (d, J=7.5H, 0.5H), and 4.05 (d, J=8 Hz, 0.5H), 4.10-4.20 (m, 1H), 4.68-4.82 (m, 2H), 5.06-5.52 (m, 2H), 5.95 (2s, 2H), 6.65 (m, 1H), 6.68 (br s, 1H), 6.75 (d, 7.5 Hz, 1H). MS (DCl/NH3) m/e 381 (M+NH4)+. Anal calcd for C18H21NO7 : C, 59.50; H, 5.82; N, 3.85. Found: C, 59.32; H, 5.71; N, 3.72. |
Here is a chemical reaction formula: Reactants are:m5:C(C)(=O)C1=CC=CC=C1;m4:C(C)(=O)O;m3_m6:CC(=O)C1=CC=C(C=C1)OC;m7_m2:C(OCC)(OCC)=O;m1_m11:[H-].[Na+], Reagents are:m8:C1(=CC=CC=C1)C;m12:O;m10:C1(=CC=CC=C1)C;m9:C1(=CC=CC=C1)C;m3_m6:C1(=CC=CC=C1)C;m7_m2:C1(=CC=CC=C1)C;m1_m11:C1(=CC=CC=C1)C, and Products are 0:COC1=CC=C(C=C1)C(CC(=O)OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Simultaneous reactions were run in both a 65-L reactor and a 35-L reactor that share the same reflux system. A nitrogen atmosphere was maintained in both. 4.0 kg (100 moles) of 60% sodium hydride in mineral oil and 32 L toluene were charged into the ambient temperature reactors. The mixture was agitated for 5 minutes and allowed to settle. 20 L of the toluene solution was aspirated. 28 L of toluene was added, agitated for 5 minutes, allowed to settle and 28 L of the toluene solution was aspirated. 68 L of toluene and 8.4 L (69.7 moles) diethyl carbonate were added. The agitation was begun and the flow of Syltherm (Note 4) in reactor jackets was initiated. A solution of 5.0 kg (33.3 moles) 4-methoxyacetophenone in 12 L toluene was added over 20 minutes. When additions were complete, the jacket temperature was reduced to 10° C. and stirring continued for 16 hours. A solution of 6.7 L (117 moles) glacial acetic acid in 23 L deionized water was fed at the same rate that was previously used for the acetophenone solution. When addition was complete, agitation was stopped and the layers separated. The aqueous layer was washed once with 13 L toluene. The combined organic layers were washed twice with 6.7 L portions of 7% (w:w) aqueous sodium bicarbonate. The toluene solution was washed once with 6.7 L of 23% (w:w) aqueous sodium chloride. The organic solution was dried over 10 kg sodium sulfate, filtered, and the solvent removed on the rotary evaporator to provide the desired product. |
Here is a chemical reaction formula: Reactants are:m4_m2:C(#N)[BH3-].[Na+];m1:COC1=CC=C(C=C1)C1=NCC(C1C(=O)OCC)C1=CC2=C(C=C1)OCO2;m5_m3:Cl, Reagents are:m4_m2:CC1=C(C=C(C(=C1Br)O)Br)C2(C=3C=CC=CC3S(=O)(=O)O2)C=4C=C(C(=C(C4C)Br)O)Br;m5_m3:C(C)O, and Products are 0:COC1=CC=C(C=C1)C1NCC(C1C(=O)OCC)C1=CC2=C(C=C1)OCO2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Into a 12-L flask equipped with magnetic stirring, addition funnel, temperature probe, and nitrogen inlet was charged 0.460 kg ethyl 2-(4-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4,5-dihydro-3H -pyrrole-3-carboxylate (1.25 mol). The reaction vessel was degassed with nitrogen. Absolute 3.7 L ethanol and 1.12 L of THF were added. 31 mg bromocresol green and 94.26 g sodium cyanoborohydride (1.5 mol) were added. A solution containing 400 mL absolute ethanol and 200 mL of 12M HCl was then added. The reaction mixture was stirred for 30 minutes after addition was complete. After the starting material was consumed, 0.5 L of 7% aq. NaHCO3 was added. The reaction mixture was concentrated and diluted with 5 L ethyl acetate. The organic layer was washed twice with 2 L of 7% aq. NaHCO3 and once with 2.5 L of 23% aq. NaCl, the dried over 190 g MgSO4, filtered, and concentrated to give 447 g of the title compound as a thick yellow oil. |
Here is a chemical reaction formula: Reactants are:m2:C(C)(=O)OC1C=CC2=CC=CC=C12;m3:CC(=O)C, Reagents are:m4:P(=O)([O-])([O-])[O-], and Products are 0:C(C)(=O)O[C@H]1C=CC2=CC=CC=C12;0:[C@H]1(C=CC2=CC=CC=C12)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.0 g (5.75 mmol) of racemic 1-acetoxyindene and 57.5 mg of lipase PS (made by Amano Seiyaku Sha, derived from Pseudomonas bacterium) were suspended in 58 ml of phosphate buffer (0.1M)-acetone mixed solution (9:1 V/V) and stirred at 37° C. for 48 hours. The reaction solution was filtered on Celite to remove lipase. The liltrate was extracted with diethyl ether and the extracted solution was dried on magnesium sulfate. The solvent was removed under a reduced pressure and the residue was subjected to silica gel column chromatography (eluate:ethyl acetate-hexane, 1:10 V/V) to separate into 446 mg (yield 44.6%) of (S)-1-acetoxyindene and 350 mg (yield 46.1%) of (R)-inden-1-ol respectively. The specific rotations and optical purities thereof were as shown below. The optical purities were determined by high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V). |
Here is a chemical reaction formula: Reactants are:m2:C1(C=CC2=CC=CC=C12)O;m3:C(C)(=O)OC=C, Reagents are:m4:C(C)(C)(C)OC, and Products are 0:C(C)(=O)O[C@@H]1C=CC2=CC=CC=C12;0:[C@@H]1(C=CC2=CC=CC=C12)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 100 mg (0.76 mmol) of racemic inden-1-ol, 0.13 mg (1.15 mmol) of vinyl acetate and 75.6 mg (100 mg of racemate/mmol) of lipase PS were suspended in 10 ml of t-butylmethyl ether and stirred at 37° C. for 7 days. After the end of the reaction, the suspension was filtered off to remove lipase. The filtrate was concentrated and the residue was subjected to silica gel column chromatography (eluate: ethyl acetate-hexane, 1:10 V/V), to separate into 50 mg (yield 38.0%, optical purity 22% ee) of (R)-1-acetoxyindene and 10 mg (yield 10.0%, optical yield 22% ee) of (S)-inden-1-ol respectively. The optical purities were determined by an analysis according to high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V). |
Here is a chemical reaction formula: Reactants are:m4_m1:CC(C)([O-])C.[Na+];m2_m3:BrC(C(F)(F)F)Cl;m2_m3:C(C=C(C)C)=O, Reagents are:m4_m1:O1CCCC1, and Products are 0:BrC(C(C=C(C)C)O)(C(F)(F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Tetrahydrofuran (230 ml) and sodium t-butoxide (57.6 g; 40% w/v solution in dimethylformamide) was charged to a split-neck reaction flask, and cooled to -60° C. with stirring. 1-Bromo-1-chloro-2,2,2-trifluorethane (47.6 g) and senecialdehyde (20.9 g) were charged simultaneously over 25 minutes, then the mixture was stirred at -60° C. for a further 30 minutes. On completion of reaction, the mass was quenched by controlled addition of saturated ammonium chloride solution (120 ml). Hexane (500 ml) was added to the mixture, then the aqueous phase was separated and extracted with further hexane (2×500 ml). The combined organics were washed with brine (2×100 ml) and then water (3×20 ml). Drying (sodium sulphate) and concentration in vacuo then gave the product 5-bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene as a mobile yellow oil (50.1 g, 70% yield). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrC(C(C=C(C)C)O)(C(F)(F)F)Cl;m1_m2_m3:C(C)(OC)(OC)OC, Reagents are:m1_m2_m3:O.[O-2].[O-2].[O-2].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.[Al+3].[Al+3], and Products are 0:BrC(C=CC(CC(=O)OC)(C)C)(C(F)(F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5-Bromo-5-chloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (10.0 g), trimethyl orthoacetate (16.0 g) and Montmorillonite KSF (0.5 g) were charged to a round-bottomed flask fitted with: nitrogen inlet/bubbler, thermometer and still-head. The mixture was heated with agitation, and the methanol-trimethyl orthoacetate distillates were collected until the reactor temperature increased to 111° C. (ca. 1 hr). The reaction was then heated to 135° C. and held for a further 1 hour. The methanol/trimethyl orthoacetate distillates were recharged and the distillation procedure repeated twice. Once the reaction was complete, the Montmorillonite was removed by filtration. The residual trimethyl orthoacetate was then removed by distillation under vacuum (ca. 50° C. @ 100 mmHg) to give the product, methyl 6-bromo-6-chloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate as a brown oil (7.8 g, 59% yield). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(OCC)(OCC)OCC;m1_m2_m3:ClC(C(C=C(C)C)O)(C(F)(F)F)Cl;m1_m2_m3:C(C(C)C)(=O)O, Reagents are:, and Products are 0:ClC(C=CC(CC(=O)OCC)(C)C)(C(F)(F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of triethyl orthoacetate (25 ml), 5,5-dichloro-4-hydroxy-2-methyl-6,6,6-trifluorohex-2-ene (3.5 g), and isobutyric acid (0.11 g) was heated at the reflux temperature. The refluxing volatiles were condensed and collected in a Dean & Stark apparatus containing molecular sieves (4A) to collect the by-product ethanol and separate it from the orthoacetate which was returned to the mixture. After 30 minutes the more volatile components were removed by evaporation under reduced pressure and the residual oil (consisting principally of 5,5-dichloro-4-(1,1-diethoxyethoxy)-2-methyl-6,6,6-trifluorohex-2-ene, 3.8 g) collected. This was then heated with isobutyric acid (10 μl) at the reflux temperature for 16 hours under a condenser containing molecular sieves (4A) to remove ethanol from the condensate. The residual oil was subjected to purification by column chromatography using a 15:1 (by volume) mixture of hexane:ethyl acetate as eluant and a silica gel column (230-400 mesh, 60 Å) to obtain ethyl 6,6-dichloro-3,3-dimethyl-7,7,7-trifluorohept-4-enoate, identified by nuclear magnetic resonance, and gas chromatographic mass-spectroscopy. |
Here is a chemical reaction formula: Reactants are:m4:C(C)(=O)OCC;m3:[OH-].[Na+];m1:C(#N)C1=CC=C(C=C1)O;m2:ClC(C(=O)[O-])(F)F.[Na+], Reagents are:m5:CN(C)C=O, and Products are 0:FC(OC1=CC=C(C#N)C=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Cyanophenol (0.50 g, 4.2 mmol, Aldrich), sodium chlorodifluoroacetate (0.77 g, 5 mmol, Alfa Products), and sodium hydroxide (0.20 g, 5 mmol) were combined in dry DMF (2 mL) under an atmosphere of argon. After stirring at 125°-130° C. for 5 h, the mixture was cooled to RT, ethyl acetate (50 mL) was added and the organic layer was washed twice with brine. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide a white solid. The solid was sublimed (1 mm Hg, 23° C.) to provide the title compound as colorless crystals (0.29 g, 41%). mp 33°-35° C. |
Here is a chemical reaction formula: Reactants are:m2:ClC(C(=O)[O-])(F)F.[Na+];m3:[OH-].[Na+];m1:[N+](=O)([O-])C1=CC=C(C=C1)O, Reagents are:m4:CN(C)C=O;m5:O, and Products are 0:FC(OC1=CC=C(C=C1)[N+](=O)[O-])F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 4-Nitrophenol (0.10 g, 0.72 mmol, Aldrich), sodium chlorodifluoroacetate (0.11 g, 0.72 mmol, Alfa Products) and sodium hydroxide (0.03 g, 0.72 mmol) were combined in dry DMF (1 mL) under an atmosphere of argon. After stirring at 125° C. for 1 h, the mixture was cooled to RT, was diluted with water and was extracted twice with ether. The combined organic extracts were washed twice with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes ) to provide the title compound as a white solid (0.10 g, 73%). mp 33°-35° C. |