Ammonia → 2-Amino-4-(benzyloxy)-2-methylbutanonitrile

HRID 1486247노트

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HRID 1486247 반응식
[C-:1]#[N:2].[Na+].[Cl-].[NH4+:5].N.[CH2:7]([O:14][CH2:15][CH2:16][C:17](=O)[CH3:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O.C(O)C.C(Cl)Cl>[NH2:5][C:17]([CH3:18])([CH2:16][CH2:15][O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:1]#[N:2]

참가 물질

8

반응물 4

HCID 222Ammonia2회HCID 8929Sodium Cyanide2회HCID 25517Ammonium Chloride2회HCID 2345114-(Benzyloxy)butan-2-one

생성물 1

HCID 583790832-Amino-4-(benzyloxy)-2-methylbutanonitrile수율 90%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매4회HCID 6344Dichloromethane용매

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온도
60 °C

실험 절차

5.31 g (108.3 mmol) of sodium cyanide in 10 ml of water were admixed with 6.37 g (119.1 mmol) of ammonium chloride (dissolved in 15 ml of warm water) and 9 ml (216.6 mmol) of conc. ammonia in water. Subsequently, 19.3 g (108.3 mmol) of 4-(benzyloxy)butan-2-one, dissolved in 3 ml of ethanol, were added. The mixture was stirred at RT for 15 min and at 60° C. for 2 h. Another 4 g (81.6 mmol) of sodium cyanide, 4.8 g (89.7 mmol) of ammonium chloride and 6.5 ml (156.4 mmol) of conc. ammonia in water were added and the mixture was stirred at 60° C. for a further 2 h. Then the reaction solution was cooled and 300 ml each of methylene chloride and water were added thereto. After phase separation, the aqueous phase was extracted with 300 ml of methylene chloride. The combined organic phases were dried and concentrated. The crude product was purified using silica gel (cyclohexane/ethyl acetate gradient 6/4-1/1). 19.9 g of the target compound (77% purity, 69% of theory) were obtained.

후처리

  1. additionwere added
  2. stirringthe mixture was stirred at 60° C. for a further 2 h
  3. temperatureThen the reaction solution was cooled
  4. customAfter phase separation
  5. extractionthe aqueous phase was extracted with 300 ml of methylene chloride
  6. customThe combined organic phases were dried
  7. concentrationconcentrated
  8. customThe crude product was purified

출처 및 근거

ORD 기록
ord-bf712c3c974646e6803ffd58272912e2
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

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