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

HRID 2053545

Reaction equation

HRID 2053545 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.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Cl)=[CH:22][CH:21]=1>CCO>[ClH:19].[Cl: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 77231-Chloro-4-(chloromethyl)benzeneHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685699342-[(4-Chlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-chlorobenzyl chloride (0.253 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 151 mg of the product 200. 1H NMR (DMSO-d6) δ 11.30 (s, 2H), 7.75-7.60 (d, 2H), 7.60-7.55 (d, 2H), 7.20-6.90 (m, 6H), 6.85-6.65 (m, 4H), 5.78 (s, 2H), 4.90 (s, 2H); MS: m/z 379 (M++1).

Workup

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

Sources & evidence

ORD record
ord-3f636c0f26b848efa958208ec1da3d2b
Source dataset
uspto-grants-2008_02
Patent number
US07326792B2

Linked notes

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