Formic Acid → N-(2-Chloro-3-fluorophenyl)formamide

HRID 1485978

반응식

HRID 1485978 반응식
C(O[C:5](=[O:7])C)(=O)C.C(O)=O.[Cl:11][C:12]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14]>>[Cl:11][C:12]1[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:13]=1[NH:14][CH:5]=[O:7]

참가 물질

4

반응물 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 888842-Chloro-3-fluoroaniline

생성물 1

HCID 57346568N-(2-Chloro-3-fluorophenyl)formamide수율 95.1%

반응 조건

온도
60 °C

실험 절차

A solution of acetic anhydride (10 mL, 106 mmol) and formic acid (30 mL, 795 mmol) was stirred at room temperature for 10 mins. 2-Chloro-3-fluoroaniline (2.9 g, 20 mmol) was added and the reaction mixture was stirred at 60° C. for 1.5 h. After cooling to room temperature, the solvents were removed in vacuo and the residue was redissolved in DCM (100 mL) and was washed with sat aq. NaHCO3 until the aqueous phase had a measured pH of 8. The organic layer was further washed with water (2×100 mL), separated and dried over MgSO4. Filtration and concentration in vacuo gave N-(2-chloro-3-fluoro-phenyl)-formamide (3.3 g, 95%) as a colorless solid which did not require further purification. MS (M+H)+: 173.9, tR=2.04 min (method 1).

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were removed in vacuo
  3. dissolutionthe residue was redissolved in DCM (100 mL)
  4. washwas washed with sat aq. NaHCO3 until the aqueous phase
  5. washThe organic layer was further washed with water (2×100 mL)
  6. customseparated
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration in vacuo

출처 및 근거

ORD 기록
ord-80cb2c5ae29045f6bce3b7a85e873dce
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422310B2

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