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

HRID 2053581

Reaction equation

HRID 2053581 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][C:23]([CH2:24][Cl:25])=[CH:22][CH:21]=1>CCO>[ClH:25].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][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:22][CH:21]=1

Participants

4

Reactant 2

HCID 68528p-Bromobenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685683962-[(4-Bromobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-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 290 mg of the product 237. 1H NMR (DMSO-d6) δ 11.30 (s, 2H), 7.65 (d, 2H), 7.58 (d, 2H), 7.15-6.95 (m, 6H), 6.90-6.65 (m, 4H), 5.78 (s, 2H), 4.80 (s, 2H); MS: m/z 424 (M++1).

Workup

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

Sources & evidence

ORD record
ord-8f3c2ad9a46049748b34122893b4e9d2
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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