Реакция #1726692

Уравнение реакции

5A

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

thionyl chloride

→

5B

Выход 80.2%

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

Выход 80.2%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураthe mixture was cooled in an ice bath
2. 2
   ДругоеThe cooling bath was removed after 30 min
3. 3
   workup.STIRRINGThe mixture was stirred for 2.5 h
4. 4
   Другоеevaporated to dryness
5. 5
   ДругоеThe residue was purified by column chromatography
6. 6
   Промывкаeluting with dichloromethane

Методика

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]+.

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