反応 #1726692

反応方程式

5A

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

thionyl chloride

→

5B

収率 80.2%

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

収率 80.2%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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]+.

出典