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

HRID 18759

Reaction equation

HRID 18759 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.[C:19]1([C:25]2[CH:32]=[CH:31][C:28]([CH2:29][Cl:30])=[CH:27][CH:26]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCO>[ClH:30].[C:19]1([C:25]2[CH:26]=[CH:27][C:28]([CH2:29][S:18][C:9]3[NH:8][C@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C@H:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:10]=3)=[CH:31][CH:32]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 154634-Phenylbenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685696462-[(4-Phenylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 57.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-phenylbenzyl chloride (0.318 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 205 mg of the product 207. 1H NMR (DMSO-d6) δ 11.24 (s, 2 H), 7.90-7.60 (m, 6 H), 7.60-7.30 (m, 3 H), 7.20-6.90 (m, 6 H), 6.90-6.65 (m, 4 H), 5.79 (s, 2 H), 4.85 (s, 2 H); MS: m/z 421 (M++1).

Workup

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

Sources & evidence

ORD record
ord-d17cb356b22f4e98b41cd409b4b17ea9
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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