تفاعل #75359

معادلة التفاعل

water

Sodium hydride

4,4'-dichlorobenzophenone oxime

chloroacetamide

→

di-(4-chlorophenyl)methyleneamino-oxyacetamide

المردود 35.4%

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىthe temperature below 30° C
2. 2
   أخرىthe temperature below 30° C
3. 3
   استخلاصthe subsequent mixture extracted with ether
4. 4
   استخلاصThe combined extract
5. 5
   غسيلwas washed with water
6. 6
   تجفيفdried (MgSO4)
7. 7
   أخرىevaporated
8. 8
   workup.ADDITIONThe residue (2.5 g.) was added to a column of dry chromatographic silica-gel [300 g
9. 9
   workup.ADDITION, previously deactivated by addition of 10% w/w water
10. 10
    workup.ADDITIONequilibrated with 10% v/w of a mixture of toluene and acetone (10:1 v/w)]
11. 11
    غسيلThe column was then eluted with the same mixture of toluene and acetone
12. 12
    أخرىto give
13. 13
    أخرىafter evaporation of solvent
14. 14
    أخرىThe solid was recrystallised from ethyl acetate/petrol

الإجراء التجريبي

Sodium hydride (0.5 g., 50% w/w suspension in mineral oil) was added gradually to a stirred solution of 4,4'-dichlorobenzophenone oxime (2.6 g.) in dry dimethylformamide (20 ml.) keeping the temperature below 30° C. After 30 minutes, chloroacetamide (0.9 g.) was added to the stirred solution keeping the temperature below 30° C. After 16 hours stirring at ambient temperature the mixture was poured into water (100 ml.) and the subsequent mixture extracted with ether. The combined extract was washed with water, dried (MgSO4) and evaporated. The residue (2.5 g.) was added to a column of dry chromatographic silica-gel [300 g., previously deactivated by addition of 10% w/w water and then equilibrated with 10% v/w of a mixture of toluene and acetone (10:1 v/w)]. The column was then eluted with the same mixture of toluene and acetone to give, after evaporation of solvent, a solid residue (1.5 g.). The solid was recrystallised from ethyl acetate/petrol giving di-(4-chlorophenyl)methyleneamino-oxyacetamide m.p. 141°-142° C. (1.1 g.) in 34% overall yield.

المصدر