Reaktion #63844

Reaktionsgleichung

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

Ausbeute 53.6%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle