p-Trifluoromethylbenzyl chloride → 2-[(4-Trifluoromethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride
Reaction equation
[C:1]1([C@H:7]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:10][C:9](=[S:18])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:30])([F:29])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][Cl:26])=[CH:23][CH:22]=1>CCO>[ClH:26].[F:19][C:20]([F:29])([F:30])[C:21]1[CH:28]=[CH:27][C:24]([CH2:25][S:18][C:9]2[NH:8][C@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=2)=[CH:23][CH:22]=1Participants
4
Procedure
A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-trifluoromethylbenzyl chloride (0.232 mL, 1.57 mmol) in abs. EtOH (2 mL) is heated at 95° C. for 24 h. The reaction mixture is cooled to RT, evaporated to dryness, and the residue suspended in Et2O. The insoluble material is filtered to give 262 mg of the product 228. 1H NMR (DMSO-d6) δ 11.42 (s, 2 H), 7.95-7.90 (m, 4 H), 7.15-6.90 (m, 6 H), 6.90-6.65 (m, 4 H), 5.77 (s, 2 H), 4.92 (s, 2 H); MS: m/z 413 (M++1).