1-Chloromethylnaphthalene → 2-[(Naphthalen-1-yl)methylthio]-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.[Cl:19][CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>CCO>[ClH:19].[C:21]1([CH2:20][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)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1Participants
4
Procedure
A mixture of intermediate 25 (200 mg, 0.786 mmol) and 1-chloromethylnaphthalene (0.277 mg, 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 67 mg of the product 213. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 8.40-8.25 (m, 1 H), 8.10-7.90 (m, 2 H), 7.90-7.80 (m, 1 H), 7.80-7.50 (3, H), 7.20-6.70 (m, 10 H), 5.79 (s, 2 H), 4.85 (s, 2 H); MS: m/z 395 (M++1).