[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].[H][H].[F:27][C:28]([F:37])([F:36])[C:29]1[CH:35]=[CH:34][C:32](N)=[CH:31][CH:30]=1.N([O-])=O.[Na+].Cl>CN(C)C=O.[Cu]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:32]3[CH:34]=[CH:35][C:29]([C:28]([F:37])([F:36])[F:27])=[CH:30][CH:31]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=16.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is dissolved in 150 ml of absolute dimethylformamide and combined with 0.60 g of sodium hydride (80% in oil). After the evolution of hydrogen has ceased, the solution is cooled to 0°, combined with a pinch of powdered copper, and then a diazonium salt solution, cooled to 0° and prepared from 3.26 g of 4-trifluoromethylaniline (99%), 1.38 g of sodium nitrite, as well as 10 ml of 6N hydrochloric acid, is added dropwise to the reaction mixture. The latter is agitated for 30 minutes at 0° and then allowed to warm up to room temperature. The solution is then concentrated under vacuum, the residue is distributed between water and ethyl acetate; the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is chromatographed on 500 g of aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate 3:2 as the eluting agent. Elution yields 3.39 g of 4,5-bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole, mp 179°-181°.
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