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Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)C1=CC(=C(C=C1)Cl)Cl, amount is: 0.0 ;m1_m2_m3_m4:BrN1C(CCC1=O)=O, amount is: 0.0 ;m1_m2_m3_m4:C(N(C)C)#N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(Cl)(Cl)(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrCC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)C1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A mixture of 5.0 g of 3,4-dichlorophenyl 4'-methyl-4-biphenylyl ketone, 2.7 g of N-bromosuccinimide and 20 mg of azaisobutyronitrile in 70 ml of carbon tetrachloride is heated to boiling under reflux. The precipitated material is filtered and the filtrate is evaporated. The residue is recrystallized from toluene/cyclohexane. 3,4-Dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone is obtained.

Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:BrCC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)C1=CC(=C(C=C1)Cl)Cl, amount is: 0.0 ;m1_m2_m3_m4:C(C=C)CN, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.ClC=1C=C(C=CC1Cl)C(=O)C1=CC=C(C=C1)C1=CC=C(C=C1)CNCCC=C, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 1.0 g of 3,4-dichlorophenyl 4'-bromomethyl-4-biphenylyl ketone, 1.5 ml of N-allylmethylamine and 0.84 g of potassium carbonate in 25 ml of ethanol are heated to boiling under reflux for 4 hours. The mixture is evaporated and the residue is extracted with ether. The extracts are dried over magnesium sulfate and treated with an ethereal hydrogen chloride solution. The precipitated hydrochloride is filtered and dried. 4'-[(Allylmethylamino)methyl]-4-biphenylyl 3,4-dichlorphenyl ketone hydrochloride, m.p. 160° C., is obtained.

Here is a chemical reaction formula: Reactants are m1:C(CCC)[Li], amount is: 0.0 ;m3_m5:CON(C(CC1=CC(=C(C=C1)O[Si](C)(C)C)F)=O)C, amount is: 0.0 ;m2_m4:BrC1=CC=C(C=C1)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:C1CCOC1, amount is: 0.0 ;m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC1=CC=C(C=C1)C(CC1=CC(=C(C=C1)O)F)=O, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A solution of 45 ml of n-butyllithium (1.6M in hexane) is added dropwise to a suspension, cooled to -78° C., of 18.2 g of 1,4-dibromobenzene in 140 ml of THF. Then, 10 g of N-methoxy-N-methyl-2-(3-fluoro-4-trimethylsilanyloxy-phenyl)-acetamide (paragraph Bb)) in 35 ml of THF are added dropwise at -78° C. The reaction mixture is stirred at -78° C. for 2 hours, then left to stand at room temperature for 1 hour while stirring. After dilution with ethyl acetate, the mixture is washed with 10% aqueous KHSO4 solution, saturated NaHCO3 solution and 10% aqueous NaCl solution. After extraction with ethyl acetate, the organic phases are dried and concentrated. Then, the silyl group is cleaved with 105 ml of THF, 11 ml of H2O and 5 drops of 1N HCl. Concentration, dissolution in methylene chloride, drying and column chromatography over silica gel with methylene chloride/0.5% methanol as the eluent, give 9.2 g of 1-(4-bromo-phenyl)-2-(3-fluoro-4-hydroxyphenyl)-ethanone. MS: m/e 308 (M+, 1 Br).

Here is a chemical reaction formula: Reactants are m1_m3_m2:FC1=C(C(=CC=C1)F)C(=O)C1=CC(=C(C=C1)OC)F, amount is: 0.0 ;m1_m3_m2:Br, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(=CC=C1)F)C(=O)C1=CC(=C(C=C1)O)F, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A solution of 3.9g of (2,6-difluoro-phenyl)-(3-fluoro-4-methoxy-phenyl)-methanone (paragraph Hd)) in 30 ml of acetic acid is stirred with 20 ml of aqueous 62% HBr solution at 125° C., then evaporated, reevaporated with toluene and taken up in ethyl acetate. The organic phase is washed with sat. aqueous NaHCO3 solution and 10% NaCl solution and then dried. 3.6 g of (2,6-difluoro-phenyl)-(3-fluoro-4-hydroxy-phenyl)-methanone MS: m/e 252 (M+), are obtained.

Here is a chemical reaction formula: Reactants are m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m2_m3:BrCCC1=CC=CC=C1, amount is: 0.0 ;m1_m4:BrC1=CC=C(C(C=O)=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=CC(=C(C=O)C1)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 66.02 g of 5-bromosalicylaldehyde was dissolved in 260 ml of N,N-dimethylformamide. Then 113.35 g of anhydrous potassium carbonate and 111.71 ml of (2-bromoethyl)benzene were added thereto and the resulting mixture was stirred at room temperature for 38 hours. After evaporation of the solvent under reduced pressure, ethyl acetate and water were added to the residue and the mixture was separated. The organic layer was collected and dried over anhydrous sodium sulfate. After evaporation of the solvent under reduced pressure, the residue was recrystallized from isopropanol to give 82.62 g of 5-bromo-2-(2-phenylethoxy)benzaldehyde. m.p. 79°-80° C.

Here is a chemical reaction formula: Reactants are m1:ClC=1C=CC(=C(C=CC(=O)OCC)C1)OCCC1=CC=CC=C1, amount is: 0.0 ;m2:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:C(C)(=O)OCC, amount is: 0.0 ,Catalysts are m4:[Pt](=O)=O, amount is: 0.0 .Products are 0:ClC=1C=CC(=C(C1)CCC(=O)OCC)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 570 mg of platinum dioxide was suspended in a solution of 11.39 g of the crude ethyl 5-chloro-2-(2-phenylethoxy)cinnamate in 80 ml of ethyl acetate and stirred in a hydrogen gas stream at room temperature for 4.5 hours. Filtering through Celite and evaporating under reduced pressure gave 10.76 g of crude ethyl 3-[5-chloro-2-(2-phenylethoxy)phenyl]propionate. This compound was not purified any more but used in the subsequent reaction as such.

Here is a chemical reaction formula: Reactants are m1_m2_m5:[H-].[Li+].[Al+3].[H-].[H-].[H-], amount is: 0.0 ;m1_m2_m5:ClC=1C=CC(=C(C1)CCC(=O)OCC)OCCC1=CC=CC=C1, amount is: 0.0 ;m3:N, amount is: 0.0 MOLE;m4:[H][H], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m7:C(C)(=O)OCC, amount is: 0.0 MOLE;m1_m2_m5:O1CCCC1, amount is: 0.0 ;m6:CCCCCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C1)CCCO)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 1.84 g of aluminum lithium hydride was added to a solution of 10.76 g of the crude ethyl 3-[5-chloro-2-(2-phenylethoxy)phenyl]propionate in 100 ml of tetrahydrofuran under ice-cooling and the mixture was stirred at the same temperature for 1 hour. Then 25% aqueous ammonia was added thereto until no hydrogen gas evolved any more. After filtering with the use of Celite and anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:9) to give 3.31 g of 3-[5-chloro-2-(2-phenylethoxy)phenyl]propanol.

Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:S(=O)(Cl)Cl, amount is: 0.0 ;m1_m2_m3_m5:ClC=1C=CC(=C(C1)CCCO)OCCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5:CN(P(N(C)C)(N(C)C)=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(C=C1)OCCC1=CC=CC=C1)CCCCl, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 1.22 ml of thionyl chloride was added to a solution of 3.24 g of 3-[5-chloro-2-(2-phenylethoxy)phenyl]propanol and 5 ml of hexamethylphosphoric triamide in 25 ml of tetrahydrofuran under ice-cooling and stirred at room temperature for 2 hours. The reaction mixture was poured into water (100 ml), extracted with ethyl acetate, successively washed with water twice and a saturated aqueous solution of sodium hydrogencarbonate 4 times and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 3.21 g of crude 4-chloro-2-(3-chloropropyl)-1-(2-phenylethoxy)benzene was obtained. This compound was not purified any more but used in the subsequent reaction.

Here is a chemical reaction formula: Reactants are m1_m2:ClC1=CC(=C(C=C1)OCCC1=CC=CC=C1)CCCCl, amount is: 0.0 ;m1_m2:C(CC)NCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CC)N(CCC)CCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: To 604 mg of the crude 4-chloro-2-(3-chloropropyl)-1-(2-phenylethoxy)benzene, was added 5 ml of di-n-propylamine and the resulting mixture was stirred at 120° C. for 39 hours. After diluting with methylene chloride, the mixture was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:5) to give 0.50 g of N,N-di-n-propyl-3-[5-chloro-2-(2-phenylethoxy)phenyl]propylamine.

Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(CC)N(CCC)CCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2_m4:C(C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)O, amount is: 0.0 ;m1_m3_m2_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)O)(=O)O.C(CC)N(CCC)CCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: To a solution of 0.50 g of N,N-di-n-propyl-3-[5-chloro-2-(2-phenylethoxy)phenyl]propylamine in 10 ml of ethanol, was added a solution of 120 mg of oxalic acid in 5 ml of ethanol. After evaporation of the solvent, the obtained crystals were recrystallized from ethyl acetate to give 380 mg of N,N-di-n-propyl-3-[5-chloro-2-(2-phenylethoxy)phenyl]propylamine oxalate.

Here is a chemical reaction formula: Reactants are m1_m4_m2_m3:ClC1=CC(=C(C=C1)OCCC1=CC=CC=C1)CCCCl, amount is: 0.0 ;m1_m4_m2_m3:[C-]#N.[K+], amount is: 0.0 ;m1_m4_m2_m3:C1COCCOCCOCCOCCOCCO1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m3:C(C)#N, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C1)CCCC#N)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: To a solution of 1.62 g of crude 4-chloro-2-(3-chloropropyl)-1-(2-phenylethoxy)benzene in 20 ml of acetonitrile, were added 681 mg of potassium cyanide and 138 mg of 18-crown-6 and heated under reflux for 11 hours. After cooling, the solvent was evaporated under reduced pressure and ethyl acetate and water were added to the residue thus obtained. Then the ethyl acetate layer was collected, washed thrice with water and a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 1.55 g of crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyronitrile was obtained. This compound was not purified any more but used in the subsequent reaction.

Here is a chemical reaction formula: Reactants are m1_m2_m3:[OH-].[K+], amount is: 0.0 MOLE;m1_m2_m3:ClC=1C=CC(=C(C1)CCCC#N)OCCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C1)CCCC(=O)O)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 15 ml of a 20% (w/v) aqueous solution of potassium hydroxide was added to a solution of 1.53 g of the crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyronitrile in 15 ml of ethanol and the resulting mixture was heated under reflux for 17 hours. After evaporation of the ethanol under reduced pressure, conc. hydrochloric acid was added dropwise to the reaction mixture until it became acidic. Then the reaction mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 1.41 g of crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyric acid was obtained. This compound was not purified any more but used in the subsequent reaction.

Here is a chemical reaction formula: Reactants are m4:[H][H], amount is: 0.0 MOLE;m3:N, amount is: 0.0 MOLE;m2_m5:ClC=1C=CC(=C(C1)CCCC(=O)O)OCCC1=CC=CC=C1, amount is: 0.0 ;m1:[H-].[Li+].[Al+3].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C1)CCCCO)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 246 mg of aluminum lithium hydride was added under ice-cooling to a solution of 1.38 g of the crude 4-[5-chloro-2-(2-phenylethoxy)phenyl]butyric acid in 20 ml of tetrahydrofuran and the resulting mixture was stirred at the same temperature for 30 minutes. Next, 25% aqueous ammonia was added thereto until no hydrogen evolved any more. After filtering with the use of Celite and anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:8) to give 0.86 g of 4-[5-chloro-2-(2-phenylethoxy)phenyl]butanol.

Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m2_m3_m5:ClC=1C=CC(=C(C1)CCCCO)OCCC1=CC=CC=C1, amount is: 0.0 ;m2_m3_m5:CN(P(N(C)C)(N(C)C)=O)C, amount is: 0.0 ;m1:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m3_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=CC(=C(C=C1)OCCC1=CC=CC=C1)CCCCCl, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 0.31 ml of thionyl chloride was added under ice-cooling to a solution of 0.86 g of 4-[5-chloro-2-(2-phenylethoxy)phenyl]butanol and 4 ml of hexamethylphosphoric triamide in 20 ml of tetrahydrofuran and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water (100 ml), extracted with ethyl acetate, successively washed with water twice and a saturated aqueous solution of sodium hydrogencarbonate 4 times and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, 0.91 g of crude 4-chloro-2-(4-chlorobutyl)-1-(2-phenylethoxy)benzene was obtained. This compound was not purified any more but used in the subsequent reaction.

Here is a chemical reaction formula: Reactants are m1_m2:ClC1=CC(=C(C=C1)OCCC1=CC=CC=C1)CCCCCl, amount is: 0.0 ;m1_m2:C(CC)NCCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C(Cl)Cl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(CC)N(CCC)CCCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: To 0.91 g of the crude 4-chloro-2-(4-chlorobutyl)-1-(2-phenylethoxy)benzene, was added 10 ml of di-n-propylamine and the resulting mixture was stirred at 120° C. for 38 hours. After diluting with methylene chloride, the mixture was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:6) to give 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine. To a solution of 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine in 10 ml of ethanol, was added a solution of 123 mg of oxalic acid in 5 ml of ethanol. After evaporation of the solvent under reduced pressure, the obtained crystals were recrystallized from ethyl acetate to give 421 mg of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine oxalate.

Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:C(CC)N(CCC)CCCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, amount is: 0.0 ;m1_m3_m2_m4:C(C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C(C)O, amount is: 0.0 ;m1_m3_m2_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)O)(=O)O.C(CC)N(CCC)CCCCC1=C(C=CC(=C1)Cl)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: To 0.91 g of the crude 4-chloro-2-(4-chlorobutyl)-1-(2-phenylethoxy)benzene, was added 10 ml of di-n-propylamine and the resulting mixture was stirred at 120° C. for 38 hours. After diluting with methylene chloride, the mixture was successively washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the obtained residue was subjected to silica gel column chromatography (developing solvent; ethyl acetate:n-hexane =1:6) to give 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine. To a solution of 1.07 g of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine in 10 ml of ethanol, was added a solution of 123 mg of oxalic acid in 5 ml of ethanol. After evaporation of the solvent under reduced pressure, the obtained crystals were recrystallized from ethyl acetate to give 421 mg of N,N-di-n-propyl-4-[5-chloro-2-(2-phenylethoxy)phenyl]butylamine oxalate.

Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:Cl.C(CC)NCCC1=CC(=C(C=C1)OC)OCCC1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m5:BrCCCCCC, amount is: 0.0 ;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.C(CCCCC)N(CCC)CCC1=CC(=C(C=C1)OC)OCCC1=CC=CC=C1, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 432 mg of N-n-propyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride, 0.87 ml of 1-bromo-n-hexane and 379 mg of anhydrous potassium carbonate were stirred in 4.4 ml of N,N-dimethylformamide at room temperature for 2 days. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and filtered, followed by evaporation of the solvent under reduced pressure. The residue was subjected to silica gel chromatography (developing solvent; n-hexane:ethyl acetate=1:1). The target fraction was concentrated and dissolved in 2 ml of ethyl acetate. After adding 0.25 ml of a 4N solution of hydrogen chloride in ethyl acetate, the solvent was evaporated to give 358 mg of oily N-n-hexyl-N-n-propyl-2-[4-methoxy-3-(2-phenylethoxy)phenyl]ethylamine hydrochloride.

Here is a chemical reaction formula: Reactants are m2:BrC=1C=C(C(=CC1)C)C, amount is: 0.0 ;m4_m5:[OH-].[K+], amount is: 0.0 ;m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1:CC1=C(C=C(C=C1)NC(=O)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:C(C)O, amount is: 0.0 ,Catalysts are m6:O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2], amount is: 0.0 .Products are 0:CC1=C(C=C(C=C1)NC2=CC(=C(C=C2)C)C)C, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: In a 2-liter three-neck flask were placed 120 g of 3,4-dimethylacetanilide synthesized in Example 1 (1), 253 g of unpurified 4-bromo-o-xylene (purity about 70%, containing about 30% 3-bromo-o-xylene), 122 g of anhydrous potassium carbonate and 2 g of copper sulfate pentahydrate, and after carrying out the reaction for 60 hours at 200° C. under a nitrogen gas stream, the reaction mixture was cooled to room temperature. To the reaction mixture was added a solution obtained by dissolving 120 g of potassium hydroxide in 600 ml of ethanol, and the mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, and then, inorganic salts were removed by filtration, and the solvent was distilled off from the filtrate under reduced pressure. The remaining filtrate was recrystallized from methanol under reduced pressure (about 155° C./0.2 mmHg) to provide 117 g of 3,3',4,4'-tetramethyldiphenylamine. (Melting point 80° to 82° C., colorless crystals) (2) Synthesis of 3,3',4,4',4"-pentamethyltriphenylamine (CT-13)

Here is a chemical reaction formula: Reactants are m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m2:IC1=CC=C(C=C1)C1=CC=CC=C1, amount is: 0.0 ;m1:CC1=C(C=C(C=C1)NC2=CC(=C(C=C2)C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CCCCCCCCCCCCC, amount is: 0.0 ,Catalysts are m4:O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2], amount is: 0.0 .Products are 0:CC=1C=C(C=CC1C)N(C1=CC=C(C=C1)C1=CC=CC=C1)C1=CC(=C(C=C1)C)C, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: In a 500-ml three-neck flask were placed 31 g of 3,3',4,4'-tetramethyldiphenylamine synthesized in Example 3 (1), 40 g of 4-iodobiphenyl, 19 g of anhydrous potassium carbonate, 2 g of copper sulfate pentahydrate and 20 ml of n-tridecane, and after carrying out the reaction for 28 hours at 200° C. under a nitrogen gas stream, the reaction mixture was cooled to room temperature. The reaction mixture was subjected to a column purification (solvent: n-hexane/toluene =10/1) with activated alumina and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and ethanol to provide 37 g of N,N-bis(3,4-dimethylphenyl)biphenyl-4-amine. (Melting point 119° to 120.5° C., colorless crystals, IR spectrum shown in FIG. 4)

Here is a chemical reaction formula: Reactants are m2:IC1=CC=CC2=CC=CC=C12, amount is: 0.0 ;m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1:CC1=C(C=C(C=C1)NC2=CC(=C(C=C2)C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CCCCCCCCCCCCC, amount is: 0.0 ,Catalysts are m4:O.O.O.O.O.S(=O)(=O)([O-])[O-].[Cu+2], amount is: 0.0 .Products are 0:CC=1C=C(C=CC1C)N(C1=CC=CC2=CC=CC=C12)C1=CC(=C(C=C1)C)C, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: In 100-ml three-neck flask were placed 7.2 g of 3,3',4,4'-tetramethyldiphenylamine synthesized in Example 3 (1), 12.2 g of 1-iodonaphthalene, 5 g of anhydrous potassium carbonate, 0.5 g of copper sulfate pentahydrate and 10 ml of n-tridecane, and after carrying out the reaction for 25 hours at 200° C. under a nitrogen gas atmosphere, the reaction mixture was cooled to room temperature. The reaction mixture was subjected to a column purification (solvent: n-hexane) with activated alumina and the solvent was distilled under reduced pressure. The residue was recrystallized from ethanol to provide 4.2 g of N,N-bis(3,4-dimethylphenyl)naphthalene-1-amine. (Melting point 125° to 127° C., light yellow crystals, IR spectrum shown in FIG. 5.)

Here is a chemical reaction formula: Reactants are m3:Cl, amount is: 0.0 MOLE;m1_m2_m4_m5:C1=CC=CC=2C(C3=C(C=CC21)C=CC=C3)C(C(=O)OCC)(C(=O)OCC)NC(C)=O, amount is: 0.0 ;m1_m2_m4_m5:[OH-].[Na+], amount is: 0.0 MOLE;m1_m2_m4_m5:CO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1=CC=CC=2C(C3=C(C=CC21)C=CC=C3)NCC(=O)O, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A mixture of diethyl 2-(5H-dibenzo[a,d]cyclohepten-5-yl)-2-acetamidomalonate (20.2g, Example 1b) and sodium hydroxide (4g) in methanol (75ml) and water (75ml) was heated to reflux for 8h. To the cooled solution was added 1M-HCl until pH=6. The solution was concentrated in vacuo and acidified to pH=2 by addition of 1M-HCl. The solid which formed was collected by filtration and heated together with 6M-HCl for 3h at 100° C. The cooled solution was filtered and the residue dissolved in hot water, refiltered and to the filtrate was added aqueous ammonia until pH 7-8. The solid which formed on cooling to room temperature was collected by filtration and dried in vacuo to give 5H-dibenzo[a,d]cyclohepten-5-ylglycine. 1H NMR (360MHz, d4MeOH), δ 4.08-4.12 (1H, m), 4.35-4.39 (1H, m), 7.0-7.11 (2H, m), 7.24-7.30 (3H, m), 7.34-7.45 (5H, m).

Here is a chemical reaction formula: Reactants are m1_m2_m3:C1=CC=CC=2C(C3=C(C=CC21)C=CC=C3)NCC(=O)O, amount is: 0.0 ;m1_m2_m3:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NCCO.C1=CC=CC=2CC3=C(C=CC21)C=CC=C3, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 5-H-Dibenzo[a,d]cyclohepten-5-ylglycine (4.8g, Example 1c) was added in portions to a solution of lithium aluminium hydride (54ml of 1.0M solution) in 30ml dry THF at 0° C. The reaction was allowed to stand at room temperature overnight, quenched with 2N sodium hydroxide and poured through Celite. The filtrate was washed with water, dried over MgSO4 and solvent removed in vacuo to leave a residue which was induced to crystallised in ethyl acetate or dichloromethane to give 5H-dibenzo[a,d]cycloheptene glycinol. 1H NMR (360MHz, d4MeOH) δ 3.05-3.17 (2H, m), 3.29-3.33 (1H, m), 3.89-3.94 (1H, m), 6.90-6.97 (2H, m), 7.23-7.38 (8H, m).

Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C(=O)O)(=O)O.C1=CC=CC=2C(C3=C(CCC21)C=CC=C3)C(COCC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N, amount is: 0.0 MOLE;m1_m2_m3:BrCC(=O)OC, amount is: 0.0 MOLE;m1_m2_m3:C(C)N(CC)CC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m4:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C(=O)O)(=O)O.C(=O)(OC)CNC(COCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1C2=C(CCC3=C1C=CC=C3)C=CC=C2, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A mixture of the title product of Example 6, methyl bromoacetate (one equivalent) and triethylamine (one equivalent) were refluxed in THF for 22h. The reaction was partitioned between diethyl ether-water and the organic phase separated and dried (MgSO4). Solvent was removed in vacuo and the residue redissolved in ethanol. Oxalic acid was added, solvent removed in vacuo, and the residue recrystallised to give the title compound. mp 160°-165° C. (ethyl acetate-petroleum ether). 1H NMR (360MHz, DMSO-d6) 2.8-3.0 (2H, m), 3.2 (2H, s), 3.4-3.5 (6H, m), 3.6-3.65 (1H, m), 3.9-3.95 (1H, m), 4.5 (3H, s), 7.00-7.2 (8H, m), 7.9 (3H, s).

Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C(=O)O)(=O)O.C1=CC=CC=2C(C3=C(CCC21)C=CC=C3)C(COCC3=CC(=CC(=C3)C(F)(F)F)C(F)(F)F)N, amount is: 0.0 MOLE;m1_m3_m2:N, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C(=O)O)(=O)O.C(N)(=O)CNC(COCC1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)C1C2=C(CCC3=C1C=CC=C3)C=CC=C2, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: A solution of the product of Example 6 in 5ml methanol saturated with ammonia was sealed in a reaction vessel and left at 0° C. for 48h. Solvent was removed in vacuo, and the residue dissolved in ethanol. Oxalic acid and water were added to give the title compound. mp 120°-122° C. 1H NMR (360MHz, DMSO-d6) 2.8-3.0 (2H, m), 3.3-3.7 (6H, m), 4.2-4.6 (4H, m), 7.00-7.4 (8H, m), 7.9 (1H, s), 7.95 (2H, s).,

Here is a chemical reaction formula: Reactants are m1_m2:C(C)(C)(C)OC(=O)NC(C(=O)OCC1=CC(=CC(=C1)C)C)C1C2=CC=CC=C2C=2C=CC=CC12, amount is: 0.0 ;m1_m2:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(=O)NC(C(=O)OCC1=CC(=CC(=C1)C)C)C1C2=CC=CC=C2C=2C=CC=CC12, please give me the reaction condition of this chemical formula.

The condition of this chemical reaction is: 3,5-Dimethylbenzyl N-t-butoxycarbonyl-2-(9-fluorenyl)glycinate (Example 9d, 0.5g) was dissolved in trifluoroacetic acid (10ml) for 40 minutes then evaporated in vacuo. To a solution of the residue in pyridine (10ml) was added acetic anhydride (1ml) for 16h. The solvent was removed in vacuo and the residue crystallised from diethyl ether/petroleum ether bp 60°-80° C. to give the title compound mp 162°-164° C. Found: C, 78.19; H,. 6.26; N, 3.45. C26H25NO3 requires C,. 78.17; H, 6.30; N, 3.50%. m/z (CI+)=400 (M+H), (CI-)=398 (M-H).