Reaktion #63845

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

acetic acid anhydride

methylbenzene

→

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

Ausbeute 42.9%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux temperature
2. 2
   TemperaturAfter cooling
3. 3
   SonstigeThe solvent was evaporated in vacuo
4. 4
   workup.STIRRINGThe residue was stirred in water
5. 5
   Extraktionthe product was extracted with trichloromethane
6. 6
   SonstigeThe extract was dried
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was purified by column chromatography over silica gel
10. 10
    SonstigeThe pure fractions were collected
11. 11
    Sonstigethe eluent was evaporated
12. 12
    SonstigeThe residue was crystallized for ethanol
13. 13
    FiltrationThe precipitated product was filtered off
14. 14
    Waschenwashed with 2,2'-oxybispropane
15. 15
    Sonstigedried

Vorschrift

A mixture of 4 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, 12 parts of acetic acid anhydride and 36 parts of methylbenzene was stirred for 90 hours at reflux temperature. After cooling, 16 parts of methanol were added. The solvent was evaporated in vacuo. The residue was stirred in water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using trichloromethane as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized for ethanol. The precipitated product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 2.0 parts (42.9%) of 1-acetyl-2-[3,5-dichloro-4-[(4-chlorophenyl)cyanomethyl]phenyl]-1,6-dihydro-4-methyl-1,2,4-triazine-3,5(2H,4H)-dione; mp. 178.1° C. (compound 78).

Quelle