Cyanoacetamide → 2-(2-Amino-4-nitrophenyl)-2-cyanoacetamide

HRID 216613

反応式

HRID 216613 の反応式
CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]([NH2:12])=[O:11])#[N:8].F[C:14]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=1[NH2:16].[Cl-].[NH4+]>CN(C)C=O>[NH2:16][C:15]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:14]=1[CH:9]([C:7]#[N:8])[C:10]([NH2:12])=[O:11]

参加物

6

反応物 4

HCID 7898CyanoacetamideHCID 25517Ammonium ChlorideHCID 677852-Fluoro-5-nitroanilineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 591899362-(2-Amino-4-nitrophenyl)-2-cyanoacetamide収率 94%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
5 °C

実験手順

Potassium tert-butoxide (36 g, 0.32 mol) was added to a solution of 2-cyanoacetamide (27 g, 0.32 mol) in anhydrous N,N-dimethylformamide (700 mL), and a solution of 2-fluoro-5-nitroaniline (25 g, 0.16 mol) in anhydrous N,N-dimethylformamide (80 mL) was added dropwise thereto under ice-cooling. After the reaction mixture was stirred at 5° C. for 18 hours, it was poured into a saturated ammonium chloride aqueous solution (1.0 L) under ice-cooling. The whole was extracted with ethyl acetate (1.0 L). The organic layer was washed with water (500 mL), brine (300 mL), and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, toluene (100 mL) and dichloromethane (100 mL) were added to the residue. The precipitated solid was filtered off, and dried under reduced pressure to give the title reference compound (33 g) as a brown solid (yield 94%).

後処理

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. extractionThe whole was extracted with ethyl acetate (1.0 L)
  4. washThe organic layer was washed with water (500 mL), brine (300 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was evaporated under reduced pressure, toluene (100 mL) and dichloromethane (100 mL)
  7. additionwere added to the residue
  8. filtrationThe precipitated solid was filtered off
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-953f7f56d69d4386834a259c4141091a
出典データセット
uspto-grants-2012_06
特許番号
US08193237B2

関連ノート

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