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

HRID 216613

반응식

HRID 216613 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 591899362-(2-Amino-4-nitrophenyl)-2-cyanoacetamide수율 94%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
5 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-953f7f56d69d4386834a259c4141091a
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193237B2

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