Ethanol → HCID 20506266, compound

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][OH:13].O[CH:15]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)S([O-])(=O)=O.[Na+].C(O)C>O>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:1]=[C:15]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[N:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:3]=2[CH:4]=1

Participants

Procedure

A mixture of 40 parts of 3-[(2-amino-5-chlorophenyl)amino]-1-propanol, 87 parts of sodium α-hydroxycyclohexanemethanesulfonate and 200 parts of ethanol is stirred and refluxed for 10 minutes. The reaction mixture is diluted with water and the solvent is evaporated. The residue is extracted a few times with trichloromethane. The combined extracts are dried, filtered and evaporated. The oily residue is triturated in 2,2'-oxybispropane: a sticky tar precipitates. The 2,2'-oxybispropane is decanted and upon stirring at room temperature, the product is allowed to precipitate. It is filtered off and dried, yielding 6-chloro-2-cyclohexyl-1H-benzimidazole-1-propanol; mp. 120.1° C.