Acetic Acid → HCID 86654464, compound

HRID 552653Notes

Reaction equation

HRID 552653 reaction equation
C(O)(=O)C.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]2([C:31]([F:34])([F:33])[F:32])[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[C:20]([O:27][CH:28]([F:30])[F:29])[CH:19]=3)[CH2:14]2)[CH:9]=[C:10]([Cl:12])[CH:11]=1>O.C(OCC)(=O)C>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:15]2[CH2:14][C:13]([C:8]3[CH:7]=[C:6]([Cl:5])[CH:11]=[C:10]([Cl:12])[CH:9]=3)([C:31]([F:33])([F:34])[F:32])[O:17][N:16]=2)=[CH:19][C:20]=1[O:27][CH:28]([F:29])[F:30]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86654463HCID 86654463, compound

Product 1

HCID 86654464HCID 86654464, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a mixture of 5.0 mL of water, 1.0 mL of acetic acid and 1.22 g of reduced iron, a solution of 2.0 g of 5-(3,5-dichlorophenyl)-3-(3-difluoromethoxy-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole in 15 mL of ethyl acetate was added dropwise at 75° C. under stirring with heating. After the completion of the addition dropwise, it was stirred at the same temperature for 2.5 hours. After the completion of the reaction, the reaction mixture was subjected to hot filtration through Celite, 20 ml of water was added in the filtrate, extracted with ethyl acetate (20 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 1.7 g of the crude aimed product as yellow resinous substance. The resulting product was used as such without purification for the next step.

Workup

  1. temperaturewith heating
  2. additionAfter the completion of the addition dropwise
  3. stirringit was stirred at the same temperature for 2.5 hours
  4. customAfter the completion of the reaction
  5. filtrationthe reaction mixture was subjected to hot filtration through Celite, 20 ml of water
  6. additionwas added in the filtrate
  7. extractionextracted with ethyl acetate (20 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-bc86b103326c492e8763dec3a5af5b2a
Source dataset
uspto-grants-2011_05
Patent number
US07951828B1

Reaction notes

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