反应 #1726692

反应方程式

5A

(3-(4-(Hydroxymethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

thionyl chloride

→

5B

收率 80.2%

(3-(4-(Chloromethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

收率 80.2%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度the mixture was cooled in an ice bath
2. 2
   其他The cooling bath was removed after 30 min
3. 3
   workup.STIRRINGThe mixture was stirred for 2.5 h
4. 4
   其他evaporated to dryness
5. 5
   其他The residue was purified by column chromatography
6. 6
   洗涤eluting with dichloromethane

实验过程

5A (3.48 g, 9.47 mmol) was dissolved in dichloromethane (150 mL) and the mixture was cooled in an ice bath. While stirring, thionyl chloride (0.76 mL, 10.4 mmol) was added dropwise. The cooling bath was removed after 30 min. The mixture was stirred for 2.5 h and then evaporated to dryness. The residue was purified by column chromatography eluting with dichloromethane. There was obtained 2.93 g (80%) of 5B as a solid. 1H NMR (500 MHz, CDCl3): δ 4.22 (m, 2H), 4.57 (s, 2H), 4.65 (m, 2H), 5.14 (m, 1H), 7.29 (d, 2H), 7.36 (d, 2H), 7.53 (t, 2H), 7.59 (t, 1H), 8.16 (d, 2H), MS (APCI+) m/z 386 [M+H]+.

来源