3,5-Dimethoxybenzyl chloride → 2-[(3,5-Dimethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18758

Reaction equation

HRID 18758 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.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=1)[CH2:24][Cl:25]>CCO>[ClH:25].[CH3:30][O:29][C:27]1[CH:26]=[C:23]([CH:22]=[C:21]([O:20][CH3:19])[CH:28]=1)[CH2:24][S:18][C:9]1[NH:8][C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C@H:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1

Participants

4

Reactant 2

HCID 27583953,5-Dimethoxybenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685686242-[(3,5-Dimethoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3,5-dimethoxybenzyl chloride (0.293 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 189 mg of the product 206. 1H NMR (DMSO-d6) δ 11.37 (s, 2 H), 7.85-7.45 (m, 4 H), 7.20-6.90 (m, 6 H), 6.90-6.60 (m, 4 H), 5.78 (s, 2 H), 4.70 (s, 2 H), 3.78 (s, 6 H); MS: m/z 405 (M++1).

Workup

  1. customevaporated to dryness
  2. filtrationThe insoluble material is filtered

Sources & evidence

ORD record
ord-99474e5abe5f457192b3ed390c5cd465
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

Loading…