1-Bromo-3-(chloromethyl)benzene → 2-[(3-Bromobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18772Notes

Reaction equation

HRID 18772 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.[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][Cl:24]>CCO>[ClH:24].[Br:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][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 5230591-Bromo-3-(chloromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685681472-[(3-Bromobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 82.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 3-bromobenzyl chloride (0.201 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 298 mg of the product 220. 1H NMR (DMSO-d6) δ 11.30 (s, 2 H), 7.95-7.80 (m, 1 H), 7.75-7.50 (m, 2 H), 7.50-7.35 (m, 1 H), 7.15-6.90 (m, 6 H), 6.90-6.60 (m, 4 H), 5.78 (s, 2 H), 4.80 (s, 2 H); MS: m/z 423 (M++1).

Workup

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

Sources & evidence

ORD record
ord-cb0e32ab037f4d6fb19c85b6428f0119
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

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