Acetic Acid → HCID 59355628, compound

HRID 1627010Notes

Reaction equation

HRID 1627010 reaction equation
C(O)(=O)C.O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:30]([F:33])([F:32])[F:31])[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]([CH2:28][CH3:29])=[C:23]([N+:25]([O-])=O)[CH:24]=3)[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1>[Fe].C(O)C>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2([C:30]([F:32])([F:31])[F:33])[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][C:22]([CH2:28][CH3:29])=[C:23]([CH:24]=3)[NH2:25])[CH2:15]2)[CH:10]=[C:11]([Cl:13])[CH:12]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 59355632HCID 59355632, compound

Product 1

HCID 59355628HCID 59355628, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

An iron powder (4.33 g) was added to a mixture of acetic acid (0.5 ml), water (22 ml) and ethanol (34 ml) at room temperature, and thereto was added 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-ethylnitrobenzene (5.60 g) obtained by Reference Production Example 29 at 75° C., and the mixture was stirred at the same temperature for 3 hours. After cooling to room temperature, the reaction mixture was filtrated and washed with ethyl acetate. To the filtrate was added an aqueous saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-ethylaniline (5.20 g).

Workup

  1. customobtained by Reference Production Example 29 at 75° C.
  2. filtrationthe reaction mixture was filtrated
  3. washwashed with ethyl acetate
  4. additionTo the filtrate was added an aqueous saturated sodium hydrogen carbonate solution
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57dc10bec7454ab7930a5b91b8d6e70d
Source dataset
uspto-grants-2014_07
Patent number
US08785485B2

Reaction notes

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