Ethyl 4-chloroacetoacetate → HCID 19603681, compound

HRID 1604649Notes

Reaction equation

HRID 1604649 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[S:22])[NH2:21])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:24][C:25](=O)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:22][CH:24]=[C:25]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:21]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium BicarbonateHCID 19603751HCID 19603751, compound

Product 1

HCID 19603681HCID 19603681, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of crude 4-tert-butyl-2-[5-(thiocarbamoylmethyl)benzofuran-2-yl]thiazole (0.73 g) and ethyl 4-chloroacetoacetate (0.92 g) in ethyl acetate (30 ml) was stirred under reflux for 18 hours. After being cooled, the resulting mixture was poured into aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with ethyl acetate. The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-{[4-(ethoxycarbonylmethyl)thiazol-2-yl]methyl}benzofuran-2-yl}thiazole (0.61 g).

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in reduced pressure
  7. washeluted with ethyl acetate
  8. additionThe fractions containing object compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc2e08af22cd4875b3b83ae6e3b62e0c
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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