Acetic Acid → HCID 68680959, compound

HRID 1171083Notes

Reaction equation

HRID 1171083 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([F:9])[CH:8]=1)[NH2:5].[N+:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])([O-])=O.C([O-])([O-])O[CH2:21][CH3:22].[C:25](O)(=O)C>O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:25]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:10]=[C:21]2[CH3:22])[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69379Ethyl nitroacetateHCID 965953,5-DifluoroanilineHCID 53630039Ethylorthoformate

Product 1

HCID 68680959HCID 68680959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

3,5-Difluoroaniline (6.75 g), ethyl nitroacetate (5.85 ml), ethyl orthoformate (9.56 ml) and acetic acid (1.2 ml) were mixed, and stirred under heating at 120° C. for 1 hour. The reaction liquid was left cooled, and the precipitated solid was collected by filtration using hexane/ethanol (1/1). Ethanol (140 ml), ethyl orthoacetate (19.1 ml) and mercury(II) chloride (714 mg) were added to the obtained solid (14.3 g). With further stirring, aluminium foil (2.84 g) was added little by little. After all the aluminium foil was dissolved, this was further stirred under heat at 80° C. for 4 hours. The reaction liquid was left cooled, then poured into a mixture of ethyl acetate and water, and the precipitated solid was removed by filtration through Celite. The filtrate was extracted with ethyl acetate, the organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1) to obtain the entitled compound (8.50 g) as a pale brown solid.

Workup

  1. customThe reaction liquid
  2. waitwas left
  3. temperaturecooled
  4. filtrationthe precipitated solid was collected by filtration
  5. additionEthanol (140 ml), ethyl orthoacetate (19.1 ml) and mercury(II) chloride (714 mg) were added to the obtained solid (14.3 g)
  6. additionWith further stirring, aluminium foil (2.84 g) was added little by little
  7. dissolutionAfter all the aluminium foil was dissolved
  8. stirringthis was further stirred
  9. temperatureunder heat at 80° C. for 4 hours
  10. customThe reaction liquid
  11. waitwas left
  12. temperaturecooled
  13. customthe precipitated solid was removed by filtration through Celite
  14. extractionThe filtrate was extracted with ethyl acetate
  15. dry with materialthe organic layer was dried with magnesium sulfate
  16. concentrationconcentrated under reduced pressure
  17. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-a9c8c70635fc4b279355053b0a63565d
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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