Ethyl 4-chloroacetoacetate → HCID 178470730, compound

HRID 1377632Notes

Reaction equation

HRID 1377632 reaction equation
Cl[CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:11][C:12]1[C:16]([CH3:17])=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:14][N:13]=1>C(#N)C>[CH2:8]([O:7][C:5]([CH2:4][C:3]1[NH:11][C:12]2[N:13]([CH:2]=1)[N:14]=[C:15]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:16]=2[CH3:17])=[O:6])[CH3:9]

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetateHCID 3184464-Methyl-5-phenyl-1,2-dihydro-3H-pyrazol-3-imine

Product 1

HCID 178470730HCID 178470730, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.78 ml of ethyl 4-chloroacetoacetate was added to a solution of 1.0 g of 3-amino-4-methyl-5-phenyl-1H-pyrazole in 25 ml of acetonitrile, and then the mixture was stirred at room temperature for 4 days. At the end of this time, the crystals which separated were filtered off and the mother liquor was concentrated by evaporation under reduced pressure. The residue was partitioned between ethyl acetate and water, and the organic phase was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 80 mg of the title compound in the form of an oil.

Workup

  1. customAt the end of this time, the crystals which separated
  2. filtrationwere filtered off
  3. concentrationthe mother liquor was concentrated by evaporation under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and water
  5. washthe organic phase was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel
  9. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-54412459cda640708d74801cd8a7dce5
Source dataset
uspto-grants-1997_09
Patent number
US05665752

Reaction notes

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