Isopropanol → Nordiazepam

反応式

Br[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)=[O:4].C1N2CN3CN(C2)C[N:22]1C3.[Br-].[NH4+].C(O)(C)C>O>[Cl:20][C:17]1[CH:18]=[CH:19][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:22]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:7]=2[CH:16]=1

参加物

実験手順

Reflux 1.76 g. (0.005 moles) of 2-(2-bromoacetamido)-5-chlorobenzophenone, 2.80 g. (0.02 moles) of hexamethylenetetramine and 1.96 g. (0.020 moles) of ammonium bromide in 14 ml. of 85% (v/v) aqueous isopropyl alcohol for 2 hours. Pour the reaction mixture into water and extract with benzene. Dry the benzene solution over anhydrous sodium sulfate. Filter and evaporate to dryness. After recrystallization, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one is obtained. In thin layer chromatography the product shows a single spot (silica gel GF plates, benzene-ethyl acetate-acetic acid=18:3:1), m.p. 213°-215° C.