Ethyl 4-chloroacetoacetate → HCID 12953391, compound

HRID 2281237Notes

Reaction equation

HRID 2281237 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.Cl[CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[S:7][CH:12]=[C:13]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69484Ethyl 4-chloroacetoacetate2×HCID 7372234-Fluorothiobenzamide

Product 1

HCID 12953391HCID 12953391, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4-fluorothiobenzamide (8.94 g, 57.6 mmol) in ethanol (70 mL) was added ethyl 4-chloroacetoacetate (7.8 mL, 58 mmol). The reaction was heated at reflux for 4 hours, treated with an addition aliquot of ethyl 4-chloroacetoacetate (1.0 mL, 7.4 mmol) and refluxed for an additional 3.5 hours. The reaction was then concentrated and the residue was partitioned between ethyl acetate (200 mL) and aqueous NaHCO3 (200 mL). The organic layer was combined with a backextract of the aqueous layer (ethyl acetate, 1×75 mL), dried (Na2SO4) and concentrated. The resulting amber oil was purified by flash chromatography using a hexane/ethyl acetate gradient to afford ethyl 2-(2-(4-fluorophenyl)thiazol-4-yl)acetate as a low melting, nearly colorless solid (13.58 g, 89%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 4 hours
  3. temperaturerefluxed for an additional 3.5 hours
  4. concentrationThe reaction was then concentrated
  5. customthe residue was partitioned between ethyl acetate (200 mL) and aqueous NaHCO3 (200 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe resulting amber oil was purified by flash chromatography

Sources & evidence

ORD record
ord-7a713490660240e598306f00f22b9861
Source dataset
uspto-grants-2015_09
Patent number
US09139580B2

Reaction notes

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