Water → N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide

HRID 543574노트

반응식

HRID 543574 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH:10]([F:12])[F:11])[NH2:5].C(N(CC)CC)C.[CH3:20][C:21]1([C:24](Cl)=[O:25])[CH2:23][CH2:22]1.O>C(Cl)Cl>[F:12][CH:10]([F:11])[O:9][C:8]1[CH:7]=[CH:6][C:4]([NH:5][C:24]([C:21]2([CH3:20])[CH2:23][CH2:22]2)=[O:25])=[CH:3][C:2]=1[F:1]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 127899391-Methylcyclopropane-1-carbonyl chlorideHCID 132929114-(Difluoromethoxy)-3-fluoroaniline

생성물 1

HCID 13314707N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide수율 83.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 3-fluoro-4-difluoromethoxyaniline (1.8 g) in methylene chloride (50 ml), triethylamine (1.1 g) was added, and a solution of 1-methylcyclopropanecarbonyl chloride (1.2 g) in methylene chloride was dropwise added thereto while stirring and ice-cooling. After stirring at room temperature for 1 hour, the reaction mixture was admixed with water and extracted with ether. The extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The oily residue (2.5 g) was chromatographed on silica gel and eluted with a mixture of hexane and acetone to give N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamide (2.2 g). nD24 1.5061.

후처리

  1. temperatureice-cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. extractionextracted with ether
  4. washThe extract was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe oily residue (2.5 g) was chromatographed on silica gel
  8. washeluted with a mixture of hexane and acetone

출처 및 근거

ORD 기록
ord-98c32e5879324ad5b230caa78cffee18
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04447260

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