Methyl 4-chloroacetoacetate → HCID 22638557, compound

HRID 2416190Notes

Reaction equation

HRID 2416190 reaction equation
[CH3:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([NH2:11])=[S:10])[CH:6]=[CH:7][N:8]=1.Cl[CH2:13][C:14](=O)[CH2:15][C:16]([O:18][CH3:19])=[O:17]>CO>[CH2:2]([C:3]1[CH:4]=[C:5]([C:9]2[S:10][CH:13]=[C:14]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[N:11]=2)[CH:6]=[CH:7][N:8]=1)[CH3:1]

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 2761171Ethionamide

Product 1

HCID 22638557HCID 22638557, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethionamide (Aldrich) (1.65 g, 10.0 mmol) and methyl 4-chloroacetoacetate (Fluka) (1.41 g, 10.0 mmol) in 50 mL of anhydrous MeOH was heated at reflux for 18 h. The solvent was evaporated to give an oily residue that was purified by chromatography (gradient elution: 10-50% EtOAc in hexanes) to afford the title compound as a light brown oil. MS m/z: 263 (M+1). Calc'd for C13H14N2O2S: 262.08.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was evaporated
  4. customto give an oily residue that
  5. customwas purified by chromatography (gradient elution: 10-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-2014453ebfed4b299bfd8710bbe95500
Source dataset
uspto-grants-2004_11
Patent number
US06822097B1

Reaction notes

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