Реакция #47052

ord-88b2038d7c6b463d9e36ad62587d6f67

Уравнение реакции

S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
intermediate 25
S=C1N[C@H](c2ccccc2)[C@H](c2ccccc2)N1
cis-4,5-Diphenylimidazolidine-2-thione
COc1ccc(CCl)cc1
4-methoxybenzyl chloride
COc1ccc(CSC2=N[C@@H](c3ccccc3)[C@@H](c3ccccc3)N2)cc1.Cl
product 223
Выход 51.7%
COc1ccc(CSC2=N[C@@H](c3ccccc3)[C@@H](c3ccccc3)N2)cc1.Cl
2-[(4-Methoxybenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride
Выход 51.7%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеevaporated to dryness
  2. 2
    ФильтрацияThe insoluble material is filtered

Методика

A mixture of intermediate 25 (200 mg, 0.786 mmol) and 4-methoxybenzyl chloride (0.213 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 167 mg of the product 223. 1H NMR (DMSO-d6) δ 11.24 (s, 2 H), 7.50 (d, 2 H), 7.20-6.90 (m, 8 H), 6.90-6.65 (m, 4 H), 5.78 (s, 2 H), 4.78 (s, 2 H), 3.78 (s, 3 H); MS: m/z 375 (M++1).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07741493B2uspto-grants-2010_06