2,6-Dibromo-4-(trifluoromethoxy)aniline → Thifluzamide

HRID 1637693Notes

Reaction equation

HRID 1637693 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 86389ThifluzamideYield 98.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07a6cab0bd9845fc9563c68ec38dd3af
Source dataset
uspto-grants-2000_03
Patent number
US06043262

Reaction notes

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