Triethylamine → 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amide

HRID 910345Notes

Reaction equation

HRID 910345 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([C:30]([F:33])([F:32])[F:31])[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=3)[CH2:17]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1.[F:34][C:35]([F:39])([F:38])[CH2:36][NH2:37]>C(Cl)(Cl)Cl.O>[Cl:8][C:9]1[CH:10]=[C:11]([C:16]2([C:30]([F:33])([F:32])[F:31])[O:20][N:19]=[C:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([NH:37][CH2:36][C:35]([F:39])([F:38])[F:34])=[O:26])=[CH:23][CH:22]=3)[CH2:17]2)[CH:12]=[C:13]([Cl:15])[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 871502064-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] benzoic acid chloride

Product 1

HCID 113406964-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifluoroethyl)benzoic acid amideYield 73.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

In a solution of 0.29 g of 2,2,2-trifluoroethylamine and 0.37 g of triethylamine in 20 ml of chloroform, 1.81 g of the crude 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]benzoic acid chloride dissolved in 10 ml of chloroform was added dropwise with cooling with ice and with stirring. After the completion of addition dropwise, the mixture was continued to stir at room temperature further for 30 minutes. After the completion of the reaction, the reaction mixture was poured in 100 ml of water, and extracted with chloroform (20 ml×3), the organic phase was washed with water, dehydrated with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate, and passed through a glass filter packed with silica gel, and then the solvent was distilled off under reduced pressure. The residual solid was washed with hexane to obtain 1.05 g of the aimed product as white crystal.

Workup

  1. additionwas added dropwise
  2. temperaturewith cooling with ice
  3. additionAfter the completion of addition dropwise
  4. stirringto stir at room temperature further for 30 minutes
  5. customAfter the completion of the reaction
  6. extractionextracted with chloroform (20 ml×3)
  7. washthe organic phase was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfilter
  10. distillationthe solvent was distilled off under reduced pressure
  11. washThe residual solid was washed with hexane

Sources & evidence

ORD record
ord-b69d3e722ccc4236b90481ad5e3e4f98
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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