反应 #499169

反应方程式

sodium hydride

Thiomorpholin-3-one

4-iodo-1,2-dichlorobenzene

→

light brown oil

收率 81.0%

4-(3,4-Dichlorophenyl)-thiomorpholin-3-one

收率 81.0%

溶剂

DMF

—

hexanes

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   温度After heating at 75° C. overnight
3. 3
   其他the mixture was partitioned between ethyl acetate and 1N lithium chloride
4. 4
   过滤filtered through diatomaceous earth
5. 5
   过滤filter cake
6. 6
   洗涤The organic layers were washed with additional 1N lithium chloride, brine (saturated sodium chloride)
7. 7
   干燥dried over calcium sulfate (CaSO4)
8. 8
   浓缩Concentration in vacuo

实验过程

Under a nitrogen atmosphere in a flame-dried flask, sodium hydride (72 mg, 1.79 mmol, 60% oil dispersion) was washed with hexanes and then treated with 6 mL of anhydrous DMF, and cooled to 0° C. Thiomorpholin-3-one (200 mg, 1.71 mmol) was added in one portion with stirring. After gas evolution had stopped (ca. 30 min), 4-iodo-1,2-dichlorobenzene (700 mg, 2.56 mmol) was added, followed after 5 minutes by copper (I) bromide (490 mg, 3.42 mmol). After heating at 75° C. overnight, the mixture was partitioned between ethyl acetate and 1N lithium chloride, filtered through diatomaceous earth and combined with additional ethyl acetate washes of the diatomaceous earth filter cake. The organic layers were washed with additional 1N lithium chloride, brine (saturated sodium chloride) and dried over calcium sulfate (CaSO4). Concentration in vacuo gave 363 mg of light brown oil which was flash chromatographed (30-50% ethyl acetate in hexanes) to give a white solid, 108 mg.

来源