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

HRID 543574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543574
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 13314707N-(4-difluoromethoxy-3-fluorophenyl)-1-methylcyclopropanecarboxamideAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-98c32e5879324ad5b230caa78cffee18
Quelldatensatz
uspto-grants-1984_05
Patentnummer
US04447260

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