反应 #168741

反应方程式

Na2S2O3

(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione

NH3

Tert-Butylhydroperoxide

ammonia hydroxide

→

title compound

(R)-5-(3-Bromo-6-nitro-phenyl)-5-methyl-5,6-dihydro-2H-[1,4]oxazin-3-ylamine

溶剂

methanol

反应条件

后处理

1. 1
   萃取the product was extracted with ethyl acetate
2. 2
   洗涤The organic phases were washed with water and brine
3. 3
   干燥dried over Na2SO4
4. 4
   其他Volatiles were removed under reduced pressure

实验过程

(R)-5-(3-Bromo-5-nitro-phenyl)-5-methyl-morpholine-3-thione (2.86 g, 7.77 mmol) was dissolved in 7M NH3 in methanol (50 ml). Tert-Butylhydroperoxide (9.41 ml, 78 mmol) and ammonia hydroxide (25% sol., 21.2 ml, 136 mmol) were added and the reaction was stirred at r.t. for 2 hrs. Upon completion, 50 ml half-saturated Na2S2O3 solution was added to the reaction and the product was extracted with ethyl acetate. The organic phases were washed with water and brine, combined and dried over Na2SO4. Volatiles were removed under reduced pressure, yielding the title compound as yellowish solid. 1H-NMR (360 MHz, DMSO-d6): 8.34 (s, 1H), 8.25 (s, 1H), 8.12 (s, 1H), 5.85 (br, 2H), 4.01 (m, 1H), 3.80 (m, 1H), 3.55 (m, 1H), 1.38 (s, 3H); MS: 314 [(M+H)+].

来源