2,6-Dibromo-4-trifluoromethoxyaniline → Thifluzamide

HRID 1637693Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637693
[CH3:1][C:2]1[S:3][C:4]([C:11](Cl)=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[Br:14][C:15]1[CH:21]=[C:20]([O:22][C:23]([F:26])([F:25])[F:24])[CH:19]=[C:18]([Br:27])[C:16]=1[NH2:17]>C(#N)C>[CH3:1][C:2]1[S:3][C:4]([C:11]([NH:17][C:16]2[C:18]([Br:27])=[CH:19][C:20]([O:22][C:23]([F:26])([F:24])[F:25])=[CH:21][C:15]=2[Br:14])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Komponenten

4

Edukt 2

HCID 27367972,6-Dibromo-4-trifluoromethoxyanilineHCID 146010812-Methyl-4-(trifluoromethyl)-5-thiazolecarbonyl chloride

Produkt 1

HCID 86389ThifluzamideAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Methyl-4-trifluoromethyl-5-chlorocarbonyl thiazole 6.47 g and 2,6-dibromo-4-trifluoromethoxy aniline 8.91 g were added in acetonitrile 16.8 ml, and they were heated to reflux for 6.5 hours. Solvent was removed from the reaction mixture by distillation under a reduced pressure, and then ethyl acetate 420 ml and water 300 ml were added and they were agitated. After standing calmly, the ethyl acetate layer was collected, and washed with water, saturated sodium bicarbonate solution, and water (300 ml each) in succession. Then, after drying over anhydrous sodium sulfate, solvent was removed by distillation under a reduced pressure, to obtain thifluzamide 13.9 g.

Aufarbeitung

  1. temperaturethey were heated
  2. temperatureto reflux for 6.5 hours
  3. customSolvent was removed from the reaction mixture by distillation under a reduced pressure
  4. additionethyl acetate 420 ml and water 300 ml were added
  5. customthe ethyl acetate layer was collected
  6. washwashed with water, saturated sodium bicarbonate solution, and water (300 ml each) in succession
  7. dry with materialThen, after drying over anhydrous sodium sulfate, solvent
  8. customwas removed by distillation under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-07a6cab0bd9845fc9563c68ec38dd3af
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06043262

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