تفاعل #1726692

معادلة التفاعل

5A

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

thionyl chloride

→

5B

المردود 80.2%

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

المردود 80.2%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was cooled in an ice bath
2. 2
   أخرىThe cooling bath was removed after 30 min
3. 3
   workup.STIRRINGThe mixture was stirred for 2.5 h
4. 4
   أخرىevaporated to dryness
5. 5
   أخرىThe residue was purified by column chromatography
6. 6
   غسيلeluting with dichloromethane

الإجراء التجريبي

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]+.

المصدر