Menthyl chloroformate → 1methyl-4-menthyloxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one

반응식

[O-2].[Mg+2].[CH:3]1([CH3:16])[CH2:8][CH2:7][CH:6]([CH:9]([CH3:11])[CH3:10])[CH:5]([O:12][C:13](Cl)=[O:14])[CH2:4]1.[CH3:17][N:18]1[C:24]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=2[CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[NH:21][CH2:20][C:19]1=[O:36]>CC(C)=O>[CH3:17][N:18]1[C:24]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:23]=2[CH:22]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:21]([C:13]([O:12][CH:5]2[CH:6]([CH:9]([CH3:11])[CH3:10])[CH2:7][CH2:8][CH:3]([CH3:16])[CH2:4]2)=[O:14])[CH2:20][C:19]1=[O:36]

참가 물질

실험 절차

0.2 g. of magnesium oxide and 1.21 g. (0.0055 moles) of menthyloxycarbonyl chloride are added to a solution of 1.34 g. (0.005 moles) of 1-methyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 20 ml. of acetone, and the mixture is stirred overnight. Next day carbon is added to the mixture, the suspension is filtered, and the filtrate is evaporated to dryness. The oily residue is dissolved in 20 ml. of ethyl acetate, the solution is shaken with 3×5 ml. of 0.1 N hydrochloric acid, the organic phase is washed with water until neutral, then dried over sodium sulfate. The drying agent is filtered off, and the filtrate is evaporated. The residue is admixed with hexane, and the solids are filtered off. 0.82 g. of 1methyl-4-menthyloxycarbonyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one, melting at 144°- 144.5° C., are obtained. The obtained substance is recrystallized from a mixture of ethanol and water. Rf2 = 0.8.