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

HRID 18792

Reaction equation

HRID 18792 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.[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][Cl:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO>[ClH:30].[O:19]([C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][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)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 932913-Phenoxybenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685695192-[(3-Phenoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3-phenoxybenzyl chloride (343 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 350 mg of the product 241. 1H NMR (DMSO-d6) δ 11.25 (s, 2 H), 7.55-7.30 (m, 6 H), 7.30-7.25 (m, 1 H), 7.25-7.10 (m, 1 H), 7.15-6.90 (m, 6H), 6.90-6.70 (m, 4 H), 5.79 (s, 2 H), 4.81 (s, 2 H); MS: m/z 437 (M++1).

Workup

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

Sources & evidence

ORD record
ord-2a306ab3f06b42529fc294e67e46d6a9
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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