Acetic Acid → HCID 67163670, compound

HRID 1187990Notes

Reaction equation

HRID 1187990 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:30]([F:33])([F:32])[F:31])[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[C:20]([N+:27]([O-])=O)[CH:19]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1>O.C(OCC)(=O)C>[NH2:27][C:20]1[CH:19]=[C:18]([C:15]2[CH2:14][C:13]([C:8]3[CH:9]=[C:10]([Cl:12])[CH:11]=[C:6]([Cl:5])[CH:7]=3)([C:30]([F:33])([F:32])[F:31])[O:17][N:16]=2)[CH:26]=[CH:25][C:21]=1[C:22]([NH2:24])=[O:23]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67164906HCID 67164906, compound

Product 1

HCID 67163670HCID 67163670, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 10 mL of water, 2 mL of acetic acid and 0.52 g of reduced iron, a solution of 0.84 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-nitro benzoic acid amide in 10 mL of ethyl acetate was added dropwise at 75° C. with stirring. After the completion of the addition dropwise, it was stirred at the same temperature further for 2.5 hours. After the completion of the reaction, insoluble material was removed by hot filtration, 20 ml of water was added in the filtrate, and the organic phase was collected, and the aqueous phase was extracted with ethyl acetate (10 ml×2). The combined organic phases were washed with 10 ml of saturated sodium hydrogen carbonate aqueous solution, and then dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.80 g of the crude aimed product as yellow crystal. The resulting product was used as such without purification for the next step.

Workup

  1. additionAfter the completion of the addition dropwise
  2. stirringit was stirred at the same temperature further for 2.5 hours
  3. customAfter the completion of the reaction, insoluble material
  4. customwas removed by hot filtration, 20 ml of water
  5. additionwas added in the filtrate
  6. customthe organic phase was collected
  7. extractionthe aqueous phase was extracted with ethyl acetate (10 ml×2)
  8. washThe combined organic phases were washed with 10 ml of saturated sodium hydrogen carbonate aqueous solution
  9. dry with materialdried over saturated sodium chloride aqueous solution
  10. distillationanhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e01de6738a7e4eff97771a637bb1057b
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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