Reaktion #63846

Reaktionsgleichung

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

benzoyl chloride

→

1-benzoyl-2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-1,6-dihydro-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione

Ausbeute 20.2%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONUpon complete addition
2. 2
   SonstigeThe reaction mixture was evaporated in vacuo
3. 3
   workup.STIRRINGthe residue was stirred in water
4. 4
   ExtraktionThe product was extracted with trichloromethane
5. 5
   SonstigeThe extract was dried
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe residue was purified twice by column chromatography over silica gel
9. 9
   SonstigeThe pure fractions were collected
10. 10
    Sonstigethe eluent was evaporated in vacuo
11. 11
    SonstigeThe residue was crystallized from 8 parts of acetonitrile
12. 12
    FiltrationThe product was filtered off
13. 13
    Waschenwashed with 2,2'-oxybispropane
14. 14
    Sonstigedried

Vorschrift

To a stirred mixture of 3 parts of 2,6-dichloro-α-(4-chlorophenyl)-4-(3,4,5,6-tetrahydro-4-methyl-3,5-dioxo-1,2,4-triazin-2(1H)-yl)benzeneacetonitrile and 20 parts of pyridine were added dropwise 1.7 parts of benzoyl chloride during a period of 5 minutes at room temperature and under nitrogen atmosphere. Upon complete addition, stirring was continued overnight at room temperature. The reaction mixture was evaporated in vacuo and the residue was stirred in water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified twice by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated in vacuo. The residue was crystallized from 8 parts of acetonitrile. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 0.8 parts (20.2%) of 1-benzoyl-2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-1,6-dihydro-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione; mp. 148.4° C. (compound 79).

Quelle