2-Benzothiazolinone, hydrazone → 1-(2-Benzothiazolyl)-5-(4-chlorophenyl)-5-hydroxy-3-(3-hydroxypropyl)-2-pyrazoline

반응식

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:16])[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][OH:14])=[CH:4][CH:3]=1.[NH:17]([C:19]1[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1)[NH2:18]>N1C=CC=CC=1.CO>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[N:17]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:16])[CH2:9][C:10]([CH2:11][CH2:12][CH2:13][OH:14])=[N:18]1

참가 물질

실험 절차

6-(4-Chlorophenyl)-4,6-diketohexanol (7.2 g, 30 mM) was treated with 2-hydrazinobenzothiazole (4.96 g, 30 mM) in pyridine (5 ml) and MeOH (150 ml) at reflux for 2 hr and then allowed to stand at RT for 48 hr. The solvents were removed in vacuo and the crude residue purified by flash chromatography on silica with Et2O:Et3N (2.5%) as eluent. The title compound (1) was obtained as a pale yellow solid, (3.15 g, mp=132°-134° C.) upon recrystallization from Et2O:hexane. NMR(CDCl3) δ 3.2 (2H, C4 -H); MS, m/e 387 (M+).