반응 #63844

반응 방정식

2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α-(4-fluorophenyl)-α-methylbenzeneacetonitrile

→

2-chloro-α-(4-fluorophenyl)-α-methyl-4-(3,4,5,6-tetrahydro-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetonitrile

수율 53.6%

용매

acetic acid

반응 조건

후처리

1. 1
   온도refluxed
2. 2
   workup.ADDITIONUpon complete addition
3. 3
   workup.STIRRINGstirring
4. 4
   온도at reflux
5. 5
   여과The reaction mixture was filtered while hot and the filtrate
6. 6
   농축was concentrated in vacuo to 10 parts of its volume
7. 7
   workup.ADDITIONWater was added to the concentrate
8. 8
   여과The precipitated product was filtered off
9. 9
   기타purified by column chromatography over silica gel using
10. 10
    workup.ADDITIONa mixture of trichloromethane and methanol (95:5 by volume) as eluent
11. 11
    기타The pure fractions were collected
12. 12
    기타the eluent was evaporated in vacuo
13. 13
    기타The residue was crystallized from acetonitrile
14. 14
    여과The product was filtered off
15. 15
    세척washed with 2,2'-oxybispropane
16. 16
    기타dried

실험 절차

To a stirred and refluxed mixture of 1.5 parts of 2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-α-(4-fluorophenyl)-α-methylbenzeneacetonitrile and 75 parts of acetic acid were added portionwise 3 parts of zinc during a period of 30 minutes. Upon complete addition, stirring was continued for 3 hours at reflux. The reaction mixture was filtered while hot and the filtrate was concentrated in vacuo to 10 parts of its volume. Water was added to the concentrate. The precipitated product was filtered off and purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was crystallized from acetonitrile. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 0.8 parts (53.6%) of 2-chloro-α-(4-fluorophenyl)-α-methyl-4-(3,4,5,6-tetrahydro-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetonitrile; mp. 122.5° C. (compound 2).

출처