5-Amino-2-methylphenol → 3-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide

HRID 2190435노트

반응식

HRID 2190435 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].[C:15]([C:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24])([CH3:19])[CH3:18])#[N:16]>O1CCCC1.O>[C:15]([C:17]([C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1)=[O:24])([CH3:19])[CH3:18])#[N:16]

참가 물질

6

반응물 3

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

생성물 1

HCID 673134703-(1-cyano-1-methylethyl)-N-(3-hydroxy-4-methylphenyl)benzamide수율 94%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5-amino-2-methylphenol (3.00 g, 24.3 mmol) in tetrahydrofuran (20 mL) was added a suspension of sodium hydrogencarbonate (3.00 g, 36.5 mmol) in water (30 mL), and the mixture was vigorously stirred at room temperature. To this mixture was added dropwise a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride produced above in tetrahydrofuran (30 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hr. The aqueous layer was separated from the reaction mixture, and the organic layer was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and decolorized with activated carbon. The insoluble material was passed through a pad filled with two layers of silica gel and celite for filtration. The solvent was evaporated under reduced pressure, and the obtained solid was washed with ethyl acetate-hexane mixture to give the title compound (6.75 g, 94%) as a white powder.

후처리

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 5 hr
  3. customThe aqueous layer was separated from the reaction mixture
  4. additionthe organic layer was diluted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. additionfilled with two layers of silica gel and celite for filtration
  8. customThe solvent was evaporated under reduced pressure
  9. washthe obtained solid was washed with ethyl acetate-hexane mixture

출처 및 근거

ORD 기록
ord-85471b6a51e447f5845381f3204a5822
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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