Thioacetamide → Ethyl 2-methyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylate

HRID 244624Notes

Reaction equation

HRID 244624 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH:6]([CH:14]([CH3:16])[CH3:15])[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(O)C>[CH3:2][C:1]1[S:3][C:6]([CH:14]([CH3:16])[CH3:15])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:4]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 58356425Ethyl 3-bromo-4-methyl-2-oxopentanoate

Product 1

HCID 58356351Ethyl 2-methyl-5-(1-methylethyl)-1,3-thiazole-4-carboxylateYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of thioacetamide (158 mg) in ethanol (20 ml) was added ethyl 3-bromo-4-methyl-2-oxopentanoate (500 mg) in ethanol (0.5 ml). Molecular sieves (100 mg) were added and the mixture was heated at 80° C. for 18 h. The mixture was filtered, washing with ethanol (5 ml) and the solvent removed in vacuo. The residue triturated with DCM and the solid removed by filtration. The filtrate was concentrated to ˜5 ml and purified by column chromatography on silica gel (10 g silica), eluting with a gradient of 0-100% ethyl acetate in cyclohexane to give the title compound as a yellow oil (280 mg).

Workup

  1. additionMolecular sieves (100 mg) were added
  2. filtrationThe mixture was filtered
  3. washwashing with ethanol (5 ml)
  4. customthe solvent removed in vacuo
  5. customThe residue triturated with DCM
  6. customthe solid removed by filtration
  7. concentrationThe filtrate was concentrated to ˜5 ml
  8. custompurified by column chromatography on silica gel (10 g silica)
  9. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-6e39d18be1de4aca94da424273dadef3
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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