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

HRID 18775

Reaction equation

HRID 18775 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.[CH2:19]([O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31][Cl:32])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO>[ClH:32].[CH2:19]([O:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][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:33][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 700424-Benzyloxybenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685693802-[(4-Benzyloxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-benzyloxybenzyl chloride (365 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 194 mg of the product 224. 1H NMR (DMSO-d6) δ 11.28 (s, 2 H), 7.60-7.25 (m, 7 H), 7.20-6.95 (m, 8 H), 6.95-6.70 (m, 4 H), 5.75 (s, 2 H), 5.25 (s, 2 H), 4.80 (s, 2 H); MS: m/z 451 (M++1).

Workup

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

Sources & evidence

ORD record
ord-4c0a2b372ec346e3b4e064f2aba69575
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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