2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-alpha-(4-fluorophenyl)-alpha-methylbenzeneacetonitrile → HCID 23035207, compound

HRID 35566Notes

Reaction equation

HRID 35566 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH:10]=[N:9]2)[CH:5]=[CH:4][C:3]=1[C:16]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)([CH3:19])[C:17]#[N:18]>[Zn].C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[CH2:10][NH:9]2)[CH:5]=[CH:4][C:3]=1[C:16]([C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)([CH3:19])[C:17]#[N:18]

Participants

4

Reactant 1

HCID 137703402-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)-alpha-(4-fluorophenyl)-alpha-methylbenzeneacetonitrile

Product 1

HCID 23035207HCID 23035207, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

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).

Workup

  1. temperaturerefluxed
  2. additionUpon complete addition
  3. stirringstirring
  4. temperatureat reflux
  5. filtrationThe reaction mixture was filtered while hot and the filtrate
  6. concentrationwas concentrated in vacuo to 10 parts of its volume
  7. additionWater was added to the concentrate
  8. filtrationThe precipitated product was filtered off
  9. custompurified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated in vacuo
  13. customThe residue was crystallized from acetonitrile
  14. filtrationThe product was filtered off
  15. washwashed with 2,2'-oxybispropane
  16. customdried

Sources & evidence

ORD record
ord-e57bfa7b7b004a918c1c5a3753ec5dc9
Source dataset
uspto-grants-1988_08
Patent number
US04767760

Reaction notes

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