Benzene, 2-(chloromethyl)-1,4-dimethyl- → 2-[(2,5-Dimethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18781

Reaction equation

HRID 18781 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.[CH3:19][C:20]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:21]=1[CH2:22][Cl:23]>CCO>[ClH:23].[CH3:19][C:20]1[CH:27]=[CH:26][C:25]([CH3:28])=[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 69987Benzene, 2-(chloromethyl)-1,4-dimethyl-HCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685692182-[(2,5-Dimethylbenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,5-dimethylbenzyl chloride (0.269 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 171 mg of the product 230. 1H NMR (DMSO-d6) δ 11.20 (s, 2 H), 7.38 (s, 1 H), 7.30-7.00 (m, 8 H), 7.00-6.85 (m, 4 H), 5.82 (s, 2 H), 4.75 (s, 2 H), 2.40 (s, 3 H), 2.30 (s, 3 H); MS: m/z 373 (M++1).

Workup

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

Sources & evidence

ORD record
ord-249d9f77aeed4ee5b72f5c2609cd6ec6
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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