Reaction #47067

Reaction equation

intermediate 25

cis-4,5-Diphenylimidazolidine-2-thione

2,5-dichlorobenzyl chloride

→

product 238

Yield 49.6%

2-[(2,5-Dichlorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride

Yield 49.6%

Solvents

EtOH

Conditions

Workup

1. 1
   Otherevaporated to dryness
2. 2
   FiltrationThe insoluble material is filtered

Procedure

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 2,5-dichlorobenzyl 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 175 mg of the product 238. 1H NMR (DMSO-d6) δ 11.50 (s, 2 H), 8.00 (s, 1 H), 7.70-7.50 (m, 2 H), 7.20-7.00 (m, 6 H), 6.95-6.80 (m, 4 H), 5.81 (s, 2 H), 4.90 (s, 2 H); MS: m/z 413 (M++1).

Source