Potassium Cyanide → 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

HRID 465689ノート

反応式

HRID 465689 の反応式
[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16](Cl)=[C:15]([C:18]#[N:19])[N:14]([CH2:20]CC)[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1.[C-]#N.[K+].[C:28]([Cu])#[N:29]>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:9][C:10]#[CH:11])=[CH:6][C:5]([N:12]2[C:16]([C:28]#[N:29])=[C:15]([C:18]#[N:19])[N:14]([CH3:20])[C:13]2=[O:23])=[C:4]([F:24])[CH:3]=1

参加物

5

反応物 3

HCID 9032Potassium CyanideHCID 198752291-(4-chloro-2-fluoro-5-propargyloxyphenyl)-5-chloro-4-cyano-3-propyl-1,3-dihydro-2 H-imidazol-2-one2 回HCID 178418546HCID 178418546、化合物

生成物 1

HCID 198752171-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The product of Example 3, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-5-chloro-4-cyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (V) (0.14 9, 0.4 mmol) was stirred in 20 mL dimethylformamide. To this mixture was added KCN (0.13 g, 2.0 mmol) and the resulting mixture was heated to reflux for ten minutes, however some starting material remained. The mixture was again heated to reflux one hour with the addition of CuCN (0.18 g, 2.0 mmol). The mixture was cooled, poured onto water, and extracted three times with 50 mL ethyl acetate. The organic solution was dried over MgSO4, filtered, and evaporated, then chromatographed to give approximately 30 mg of a glassy oil. Recrystallization with ethyl ether/hexane gave 22 mg of 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4,5-dicyano-3-methyl-1,3-dihydro-2H-imidazol-2-one (VI) (m.p. 124°-6° C.).

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for ten minutes
  3. temperatureThe mixture was again heated
  4. temperatureThe mixture was cooled
  5. additionpoured onto water
  6. extractionextracted three times with 50 mL ethyl acetate
  7. dry with materialThe organic solution was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customchromatographed

出典と根拠

ORDレコード
ord-46669dfce97e4175964cf4c99511e93a
出典データセット
uspto-grants-1992_10
特許番号
US05153316

反応ノート

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