Реакция #64074

Уравнение реакции

methylamine hydrochloride

trimethylaluminum

ester

methyl bis(2-chloroethylthio)acetate

→

4c

Выход 64.0%

N-methyl-bis(2-chloroethylthio)acetamide

Выход 64.0%

Растворители

benzene

benzene

Условия реакции

Обработка

1. 1
   Другое(30 min)
2. 2
   Температураto cool to room temperature
3. 3
   Другоеwas then quenched by dropwise addition of 60 mL of 1.0 N HCl
4. 4
   ЭкстракцияThe mixture was extracted several times with ethyl acetate
5. 5
   Сушкаthe combined extracts were dried (MgSO4)
6. 6
   Концентрированиеconcentrated under vacuum

Методика

To a stirred suspension of methylamine hydrochloride (3.464 g; 0.051 mol) in 60 mL of dry benzene under nitrogen at room temperature was added trimethylaluminum (Aldrich, 25.65 mL of 2.0M solution in toluene). After gas evolution ceased (30 min) a solution of the ester 4b (4.500 g; 0.017 mol in 10 mL of dry benzene was added and the mixture was warmed to 50° C. After 21 h, the mixture was allowed to cool to room temperature and was then quenched by dropwise addition of 60 mL of 1.0 N HCl. The mixture was extracted several times with ethyl acetate and the combined extracts were dried (MgSO4) and concentrated under vacuum. Flash chromatography on silica gel (eluent: 2/3 ethyl acetate/hexanes) gave 2.849 g (64%) of 4c, mp 82°-84° C.

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