Hydrochloric Acid → 1H-Imidazole-2-propanol, 5-((3,5-dichlorophenyl)thio)-1-ethyl-4-(1-methylethyl)-
Reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]([CH2:29][CH3:30])[C:14]([S:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)=[C:15]([CH:17]([CH3:19])[CH3:18])[N:16]=1)C1C=CC=CC=1.Cl.C(=O)([O-])O.[Na+]>>[Cl:27][C:25]1[CH:26]=[C:21]([S:20][C:14]2[N:13]([CH2:29][CH3:30])[C:12]([CH2:11][CH2:10][CH2:9][OH:8])=[N:16][C:15]=2[CH:17]([CH3:18])[CH3:19])[CH:22]=[C:23]([Cl:28])[CH:24]=1Participants
4
Conditions
- Temperature
- 110 °C
Procedure
To 5.3 g (11.4 mmol) of the above oil (136b) was added 24 ml of concentrated hydrochloric acid and the mixture was heated at 110° C. for 2 hours. After cooling, the mixture was neutralized with sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water, dried over sodium sulfate, arid concentrated under reduced pressure. The residue was purified by silica gel column chromatography (3% methanol-ethyl acetate) and recrystallized from n-hexane to provide 3.2 g (yield 75%) of 3-(5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)-propan-1-ol (137b) as crystals. mp 73° C.