2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane methanesulphonate → 1-[2-(2,4-Dichlorophenyl)-2-hydroxy-3-(thiazol-2-ylthio)propyl]-1,2,4-triazole
Reaction equation
CS(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]1([CH2:17][N:18]2[CH:22]=[N:21][CH:20]=[N:19]2)[CH2:16][O:15]1.[SH:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1>C(O)(=O)C>[Cl:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[C:14]([OH:15])([CH2:16][S:23][C:24]1[S:25][CH:26]=[CH:27][N:28]=1)[CH2:17][N:18]1[CH:22]=[N:21][CH:20]=[N:19]1Participants
4
Procedure
2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane, methanesulphonate salt, (6 g, 0.0164 m) and 2-mercaptothiazole (6 g, 0.05 m) were heated in glacial acetic acid (200 ml) under refluxed for 4 hours. The solvent was then evaporated and the residue was basified with dilute sodium hydroxide solution and extracted with methylene chloride. The extract was washed once with dilute sodium hydroxide solution, dried (MgSO4) and evaporated to give a pale brown glass (5.4 g) which was chromatographed on silica, eluting with ethyl acetate:ether:methanol:diethylamine 25:75:2:2, to give, after one recrystallization from isopropanol, the title compound 2 g, (32%); m.p. 110°-111° C.