2,6-Dichlorobenzyl chloride → 2-[(2,6-Dichlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

HRID 18761

Reaction equation

HRID 18761 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][CH:25]=[C:24]([Cl:28])[C:21]=1[CH2:22]Cl>CCO>[ClH:19].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[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 748322,6-Dichlorobenzyl chlorideHCID 45258634cis-4,5-Diphenylimidazolidine-2-thione

Product 1

HCID 685707032-[(2,6-Dichlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole HydrochlorideYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,6-dichlorobenzyl chloride (0.307 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 296 mg of the product 209. 1H NMR (DMSO-d6) δ 11.47 (s, 2 H), 7.75-7.60 (m, 2 H), 7.60-7.40 (m, 1 H), 7.30-6.85 (m, 10 H), 5.90 (s, 2 H), 4.98 (s, 2 H); MS: m/z 413 (M++1).

Workup

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

Sources & evidence

ORD record
ord-a93354d747ed476bb9a00d4fab5958dc
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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