Hydrochloric Acid → HCID 13823607, compound

HRID 1748618Notes

Reaction equation

HRID 1748618 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[NH:13][NH2:14].CCOC=[CH:19][C:20](=O)[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].Cl.[CH2:29](O)C>>[CH2:25]([O:24][C:22]([C:21]1[CH:29]=[N:14][N:13]([C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8]([F:9])([F:11])[F:10])=[CH:5][C:4]=2[Cl:12])[C:20]=1[CH3:19])=[O:23])[CH3:26]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 54463595Ethyl ethoxymethyleneacetoacetate

Product 1

HCID 13823607HCID 13823607, compound

Procedure

[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazine (5 g) and ethyl (2-ethoxymethylene)acetoacetate (3.8 g) synthesized according to the method described in J. Chem. Soc. Perkin trans. I, p. 1875 (1988) were added to a mixed solvent of 1 N hydrochloric acid aqueous solution (90 ml) and ethanol (100 ml), and stirred for 4 hours under reflux. After completion of the reaction, the mixture was allowed to cool, ethanol was evaporated, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (5.83 g) as a yellow oil. MS (ESI) m/z: 367, 369 (M+H)+.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. temperatureto cool
  4. customethanol was evaporated
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated
  9. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cda14c114cfa4de3a315bf40390f1633
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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