تفاعل #64074

معادلة التفاعل

methylamine hydrochloride

trimethylaluminum

ester

methyl bis(2-chloroethylthio)acetate

→

4c

المردود 64.0%

N-methyl-bis(2-chloroethylthio)acetamide

المردود 64.0%

المذيبات

benzene

benzene

ظروف التفاعل

المعالجة

1. 1
   أخرى(30 min)
2. 2
   درجة الحرارةto cool to room temperature
3. 3
   أخرىwas then quenched by dropwise addition of 60 mL of 1.0 N HCl
4. 4
   استخلاصThe mixture was extracted several times with ethyl acetate
5. 5
   تجفيفthe combined extracts were dried (MgSO4)
6. 6
   تركيزconcentrated under vacuum

الإجراء التجريبي

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.

المصدر