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

HRID 1486247ノート

反応式

HRID 1486247 の反応式
[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]

参加物

8

反応物 4

HCID 222Ammonia2 回HCID 8929Sodium Cyanide2 回HCID 25517Ammonium Chloride2 回HCID 2345114-(Benzyloxy)butan-2-one

生成物 1

HCID 583790832-Amino-4-(benzyloxy)-2-methylbutanonitrile収率 90%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒4 回HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bf712c3c974646e6803ffd58272912e2
出典データセット
uspto-grants-2016_08
特許番号
US09422285B2

反応ノート

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