Water → HCID 22494336, compound

HRID 1816617Notes

Reaction equation

HRID 1816617 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:11]([NH2:15])(=[S:14])[CH2:12][CH3:13].O>C(O)C>[CH2:12]([C:11]1[S:14][C:8]([CH3:10])=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:15]=1)[CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 11858Ethyl 2-chloroacetoacetateHCID 2760628Propanethioamide

Product 1

HCID 22494336HCID 22494336, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.33 ml ethyl 2-chloroacetoacetate and 1.5 g thiopropionamide were dissolved in 30 ml ethanol, followed by stirring at room temperature for 16 hours. The reaction solution was ice-cooled and water was added thereto, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=14:1), to give 0.8 g of ethyl 2-ethyl-5-methyl-1,3-thiazole-4-carboxylate.

Workup

  1. temperaturecooled
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=14:1)

Sources & evidence

ORD record
ord-96d55e2770b54507ba34e6f8f0f7735e
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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