Sodium Bicarbonate → Ethyl (2-propyl-1,3-thiazol-5-yl)acetate

HRID 972835Notes

Reaction equation

HRID 972835 reaction equation
Br[CH:2]([CH2:8][CH:9]=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11]([NH2:16])(=[S:15])[CH2:12][CH2:13][CH3:14].C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH2:12]([C:11]1[S:15][C:8]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:9][N:16]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12454243ButanethioamideHCID 18668033Ethyl 2-bromo-4-oxo-butyrate

Product 1

HCID 54320013Ethyl (2-propyl-1,3-thiazol-5-yl)acetateYield 73.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 20.6 g of ethyl 2-bromo-4-oxo-butyrate, 10.9 g of thiobutyramide and 400 ml of dichloroethane was refluxed under a nitrogen atmosphere which recycling the dehydrated condensate. The mixture was cooled and then mixed with 45 ml of a saturated sodium bicarbonate aqueous solution. The mixture was decanted and the organic phase was dried and evaporated to dryness. The liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture yielded 15.4 g of ethyl 2-propyl-5-thiazole-acetate. The IR spectrum in CHCl3 showed an ester carbonyl at 1737cm-1 and C=C at 1536cm-1

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere which
  2. temperatureThe mixture was cooled
  3. customThe mixture was decanted
  4. customthe organic phase was dried
  5. customevaporated to dryness
  6. customThe liquid residue was chromatographed over silica gel and elution with a 8-2 cyclohexane-benzene mixture

Sources & evidence

ORD record
ord-7972fdc278954c5f9728ea362ee147ab
Source dataset
uspto-grants-1977_10
Patent number
US04053618

Reaction notes

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