تفاعل #1726684

معادلة التفاعل

methanesulfonyl chloride

2B

(5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl)(3-hydroxyazetidin-1-yl)methanone

methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate

Triethylamine

→

2C

المردود 75.0%

1-(5-(4-Chlorophenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

المردود 75.0%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   أخرىthe cooling bath was removed
4. 4
   أخرىThe reaction mixture was transferred to a reparatory funnel
5. 5
   غسيلwas washed with water
6. 6
   أخرىThe organic solution was dried (phase separator)
7. 7
   أخرىevaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   ترشيحthe solid product was collected by filtration
10. 10
    غسيلThe solid was washed twice with diethyl ether
11. 11
    أخرىdried in vacuo
12. 12
    أخرىThe product was purified
13. 13
    غسيلfirst eluting with dichloromethane
14. 14
    workup.ADDITIONwith a mixture of dichloromethane and methanol containing 2M NH3 (20:1)

الإجراء التجريبي

A suspension of 2B —which contained approximately 50% of methyl 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-carboxylate as an impurity—(1.38 g, 2.47 mmol) in dichloromethane (50 mL) was cooled in an ice-bath. Triethylamine (0.51 mL, 3.70 mmol) was added followed by methanesulfonyl chloride (0.27 mL, 3.45 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The reaction mixture was transferred to a reparatory funnel and was washed with water followed by aqueous NaHCO3. The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was collected by filtration. The solid was washed twice with diethyl ether and then dried in vacuo. The product was purified using flash column chromatography first eluting with dichloromethane and then with a mixture of dichloromethane and methanol containing 2M NH3 (20:1). There was obtained 0.66 g (75%) of 2C as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 4.43 (dd, 1H), 4.65 (dd, 1H), 4.87 (dd, 1H), 5.12 (dd, 1H), 5.41 (m, 1H), 7.53 (d, 2H), 8.10 (d, 2H), MS (APCI+) m/z 358 [M+H]+.

المصدر