Acetic Acid → HCID 21266769, compound

HRID 1005282Notes

Reaction equation

HRID 1005282 reaction equation
C(O)(=O)C.C(O)C.[Cl:8][C:9]1[C:14]([N+:15]([O-])=O)=[CH:13][C:12]([C:18]2[C:22]([C:23]([F:26])([F:25])[F:24])=[C:21]([C:27]([F:30])([F:29])[F:28])[N:20]([CH3:31])[N:19]=2)=[C:11]([F:32])[CH:10]=1>[Fe].C(OCC)(=O)C>[NH2:15][C:14]1[C:9]([Cl:8])=[CH:10][C:11]([F:32])=[C:12]([C:18]2[C:22]([C:23]([F:24])([F:25])[F:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[N:20]([CH3:31])[N:19]=2)[CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 702EthanolHCID 18791018HCID 18791018, compound

Product 1

HCID 21266769HCID 21266769, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4,6 g (83 mmol) of iron powder, 14 ml of glacial acetic acid and 30 ml of ethanol were heated to 70-75° C. and the mixture was treated with 7 g (17 mmol) of 3-(4-chloro-2-fluoro-5-nitrophenyl)-l-methyl-4,5-di(trifluoromethyl)-1H-pyrazole. After the mixture had been stirred for 2 hours at reflux temperature, it was treated with 100 ml of ethyl acetate. The mixture was then filtered through kieselguhr, whereupon the filtrate was washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate and finally concentrated. The residue was purified by means of silica gel chromatography (eluent: hexane/ethyl acetate=4:1). Yield: 22%.

Workup

  1. temperatureat reflux temperature, it
  2. filtrationThe mixture was then filtered through kieselguhr, whereupon the filtrate
  3. washwas washed with saturated aqueous sodium hydrogen carbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationfinally concentrated
  6. customThe residue was purified by means of silica gel chromatography (eluent: hexane/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-25e061208a514277a3c9163439364b47
Source dataset
uspto-grants-2000_04
Patent number
US06054412

Reaction notes

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