3-Amino-p-cresol → 3-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide

HRID 2190377노트

반응식

HRID 2190377 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].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>[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]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8])=[O:24])([CH3:19])[CH3:18])#[N:16]

참가 물질

5

반응물 3

HCID 178203-Amino-p-cresolHCID 516892Sodium BicarbonateHCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

생성물 1

HCID 673120273-(1-cyano-1-methylethyl)-N-(5-hydroxy-2-methylphenyl)benzamide수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a two-layer solution of 3-amino-4-methylphenol (3.25 g, 26.4 mmol) in tetrahydrofuran (20 mL)/1N aqueous sodium hydrogencarbonate solution (39 mL) was added a solution of 3-(1-cyano-1-methylethyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 3 hr. The aqueous layer was separated, and extracted with ethyl acetate (100 mL). The combined organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL), successively, and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate (45 mL)/hexane (45 mL) to give the title compound (5.95 g, 77%) as a colorless powder.

후처리

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (100 mL)
  3. washThe combined organic layer was washed with 5% aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL)
  4. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was recrystallized from ethyl acetate (45 mL)/hexane (45 mL)

출처 및 근거

ORD 기록
ord-c9ce43a800974d84827718b2e3df1c3e
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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