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

HRID 2053579Notes

Reaction equation

HRID 2053579 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:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[Br:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][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 5218161-Bromo-2-(chloromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685699152-[(2-Bromobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 110.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2-bromobenzyl chloride (327 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 400 mg of the product 235. 1H NMR (DMSO-d6) δ 11.52 (s, 2H), 7.86 (d, 1H), 7.78 (d, 1H), 7.55-7.30 (m, 2H), 7.20-7.00 (m, 6H), 7.00-6.85 (m, 4H), 5.83 (s, 2H), 4.95 (s, 2H); MS: m/z 424 (M++1).

Workup

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

Sources & evidence

ORD record
ord-b690360c49db4f8b85d7557e4922deac
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Reaction notes

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