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

HRID 2190367노트

반응식

HRID 2190367 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]1([C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23](Cl)=[O:24])[CH2:19][CH2:18]1)#[N:16]>O1CCCC1>[C:15]([C:17]1([C:20]2[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=2)[C:23]([NH:1][C:2]2[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=2[CH3:8])=[O:24])[CH2:18][CH2:19]1)#[N:16]

참가 물질

5

반응물 3

HCID 178203-Amino-p-cresolHCID 516892Sodium Bicarbonate2회HCID 866319823-(1-Cyanocyclopropyl)benzoyl chloride

생성물 1

HCID 673125693-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a two-layer solution of 3-amino-4-methylphenol (5.92 g, 48.0 mmol) in tetrahydrofuran (40 mL)/1N aqueous sodium hydrogencarbonate solution (54 mL) was added a solution of 3-(1-cyanocyclopropyl)benzoyl chloride synthesized above in tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 2 hr. Since the reaction mixture showed pH 4-5, sodium hydrogencarbonate (900 mg, 10.7 mmol) was added to adjust the pH to 8-9, and the reaction mixture was further stirred at room temperature for 1 hr. The aqueous layer was separated, and extracted with ethyl acetate (150 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. To the obtained suspension was added ethyl acetate (25 mL)/hexane (50 mL), and the mixture was stirred at room temperature for 20 min. The precipitate was collected by filtration, repeatedly washed with diisopropyl ether/hexane (1:1) and air-dried to give the title compound (12.2 g, 87%) as a pale-yellow powder.

후처리

  1. additionwas added
  2. stirringthe reaction mixture was further stirred at room temperature for 1 hr
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (150 mL)
  5. washThe combined organic layer was washed with saturated brine (150 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. additionTo the obtained suspension was added ethyl acetate (25 mL)/hexane (50 mL)
  10. stirringthe mixture was stirred at room temperature for 20 min
  11. filtrationThe precipitate was collected by filtration
  12. washrepeatedly washed with diisopropyl ether/hexane (1:1)
  13. customair-dried

출처 및 근거

ORD 기록
ord-42a42adcc6b0429c879ab8ccb68cdc4d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324395B2

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