Water → N-hydroxy-2-(4-nitrophenyl)acetamidine

HRID 30662

반응식

HRID 30662 반응식
Cl.[NH2:2][OH:3].CO.C[O-].[Na+].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]#[N:20])=[CH:14][CH:13]=1)([O-])=[O:10].[OH2:21]>CS(C)=O>[OH:3][N:2]=[C:19]([NH2:20])[CH2:18][C:15]1[CH:14]=[CH:13][C:12]([N+:9]([O-:10])=[O:21])=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 68386p-NitrophenylacetonitrileHCID 443297Hydroxyamine hydrochlorideHCID 23694274Sodium methanolate methanol

생성물 1

HCID 308292N-hydroxy-2-(4-nitrophenyl)acetamidine수율 59%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
100 °C

실험 절차

To a mixture of hydroxylamine hydrochloride (21.5 g) and dimethyl sulfoxide (50 mL) was added dropwise 28% sodium methoxide methanol solution (59.6 g) at room temperature. A solution (50 mL) of (4-nitrophenyl)acetonitrile (10.0 g) in dimethyl sulfoxide was further added dropwise to the reaction mixture. The reaction mixture was stirred at 100° C. for 3 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give N′-hydroxy-2-(4-nitrophenyl)ethanimidamide as brown crystals (7.10 g, yield 59%). Recrystallization thereof from ethyl acetate-diisopropyl ether gave brown prism crystals. melting point: 170-171° C.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-05d8c6aef45e47969bcddacab17cb55b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423159B2

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