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

HRID 1710039ノート

反応式

HRID 1710039 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 23035207HCID 23035207、化合物収率 53.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f0d130f291d45d3884f4b216ae17b99
出典データセット
uspto-grants-1990_08
特許番号
US04952570

反応ノート

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