Ethyl 2-chloroacetoacetate → HCID 59296132, compound

HRID 2233548Notes

Reaction equation

HRID 2233548 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.[CH2:12]([O:14][C:15](=[O:21])[CH:16](Cl)[C:17]([CH3:19])=O)[CH3:13]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[O:8][C:7]([C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:9][C:17]=1[CH3:19])=[O:21])[CH3:13]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 769594-Methoxybenzamide

Product 1

HCID 59296132HCID 59296132, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

40.0 g 4-Methoxybenzamide was dissolved in 400 ml ethanol. The mixture was warmed to 50° C. and 48.8 ml ethyl-2-chloroacetoacetate was added in one portion. The resulting mixture was refluxed for four days. The reaction mixture was cooled and the solvent removed under reduced pressure. The resulting residue was purified by flash chromatography on silica gel to obtain 23.5 g 2-(4-Methoxy-phenyl)-4-methyl-oxazole-5-carboxylic acid ethyl ester as a solid.

Workup

  1. temperatureThe resulting mixture was refluxed for four days
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent removed under reduced pressure
  4. customThe resulting residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-20dcb2758d4b49b89f7fbf83a7471c3d
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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