Ethyl 2-chloroacetoacetate → HCID 69280529, compound

HRID 1767970Notes

Reaction equation

HRID 1767970 reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[S:5].Cl[CH:17]([C:23]([CH3:25])=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(O)C>[CH2:21]([O:20][C:18]([C:17]1[S:5][C:4]([C:3]2[CH:7]=[CH:8][C:9]([C:12]([F:15])([F:14])[F:13])=[C:10]([F:11])[C:2]=2[F:1])=[N:6][C:23]=1[CH3:25])=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 236144852,3-Difluoro-4-(trifluoromethyl)benzene-1-carbothioamide

Product 1

HCID 69280529HCID 69280529, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2,3-difluoro-4-trifluoromethyl-thiobenzamide (1.15 g, 4.8 mmol) and ethyl 2-chloro-acetoacetate (0.67 ml, 4.8 mmol) in ethanol (70 ml) was heated at reflux temperature for 14 hours. The solvent was removed under reduced pressure and the residue partitioned between ice water and ethyl acetate. The layers were separated and the aqueous phase extracted two more times with ethyl acetate. The combined extracts were washed two times with ice water/brine 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to yield 700 mg (2 mmol, 42%) of the title compound as yellow crystals.

Workup

  1. temperatureat reflux temperature for 14 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ice water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted two more times with ethyl acetate
  6. washThe combined extracts were washed two times with ice water/brine 1/1
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customto give a yellow oil which
  10. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-eee3dc61cd5d4a0997248e0ee4608ce4
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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