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

HRID 862100노트

반응식

HRID 862100 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

(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).

후처리

  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

출처 및 근거

ORD 기록
ord-2671fda9577d4aed8dbe77c443579a8f
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05716971

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