Ethylenediamine → 4-hydroxy-3-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]benzonitrile

HRID 862100ノート

反応式

HRID 862100 の反応式
[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12](Br)[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C(N)[CH2:23][NH2:24]>CN(C=O)C.O>[C:1]([O:5]/[N:6]=[C:7](\[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)/[C:8]1[CH:13]=[C:12]([C:23]#[N:24])[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 3301EthylenediamineHCID 1364637264-bromo-2-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]phenol

生成物 1

HCID 1364637874-hydroxy-3-[(Z)-N-[(2-methylpropan-2-yl)oxy]-C-pyridin-2-ylcarbonimidoyl]benzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(Z)-2-(5-bromo-2-hydroxybenzoyl)pyridine O-t-butyloxime (12.7 g) was dissolved in DMF (100 ml). To the solution was added cuprous cyanide (4.64 g), and the mixture was heated, under argon atmosphere, for 3 hours under reflux. To the reaction mixture was added a solution of ethylenediamine (30 ml) in water (20 ml). The mixture was stirred for 30 minutes at room temperature, followed by extraction with ethyl acetate. The organic layer was dried (anhydrous magnesium sulfate), then the solvent was distilled off. The residue was purified by means of a silica gel column chromatography, eluting with ethyl acetate/hexane, to give (Z)-2-(5-cyano-2-hydroxybenzoyl)pyridine O-t-butyloxime (4.31 g) (Compound 76).

後処理

  1. temperaturethe mixture was heated, under argon atmosphere, for 3 hours
  2. temperatureunder reflux
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried (anhydrous magnesium sulfate)
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by means of a silica gel column chromatography
  7. washeluting with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-2671fda9577d4aed8dbe77c443579a8f
出典データセット
uspto-grants-1998_02
特許番号
US05716971

反応ノート

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