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

HRID 356644Notes

Reaction equation

HRID 356644 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 reflex for 6.5 hours. Solvent was removed from the reaction mixture by distillation under a reduced pressure, and then ethyl acetate 420 g and water 300 ml were added and they were agitated. After standing calmly, the ethyl acetate layer was collected, and washed with 300 ml each of water, saturated sodium bicarbonate solution, and water 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. customSolvent was removed from the reaction mixture by distillation under a reduced pressure
  3. additionethyl acetate 420 g and water 300 ml were added
  4. customthe ethyl acetate layer was collected
  5. washwashed with 300 ml each of water, saturated sodium bicarbonate solution, and water in succession
  6. dry with materialThen, after drying over anhydrous sodium sulfate, solvent
  7. customwas removed by distillation under a reduced pressure

Sources & evidence

ORD record
ord-a638014f3cda413590fe5ed092f3690a
Source dataset
uspto-grants-1998_11
Patent number
US05837721

Reaction notes

Loading…