Benzyl Chloride → 2-(Benzylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18753

Reaction equation

HRID 18753 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]([Cl:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCO>[ClH:26].[CH2:19]([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:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685694492-(Benzylthio)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and benzyl chloride (0.184 mL, 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 128 mg of the product 201. 1H NMR (DMSO-d6) δ 11.30 (s, 2H), 7.70-7.50 (m, 2 H), 7.50-7.35 (m, 3 H), 7.20-6.95 (m, 6 H), 6.90-6.70 (m, 4 H), 5.78 (s, 2H), 4.90 (s, 2 H); MS: m/z 345 (M++1).

Workup

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

Sources & evidence

ORD record
ord-c0bd3f8cfc034739a693ea7b6cd94218
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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