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

HRID 30662

反応式

HRID 30662 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05d8c6aef45e47969bcddacab17cb55b
出典データセット
uspto-grants-2008_09
特許番号
US07423159B2

関連ノート

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