2-Methylpropanethioamide → Methyl 2-isopropyl-5-methylthiazole-4-carboxylate

HRID 1689376Notes

Reaction equation

HRID 1689376 reaction equation
Br[CH:2]([CH3:9])[C:3](=O)[C:4]([O:6][CH3:7])=[O:5].[CH3:10][CH:11]([CH3:15])[C:12](=[S:14])[NH2:13]>C1COCC1>[CH:11]([C:12]1[S:14][C:2]([CH3:9])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[N:13]=1)([CH3:15])[CH3:10]

Participants

4

Reactant 2

HCID 109095072-MethylpropanethioamideHCID 11183175Methyl 3-bromo-2-oxobutanoate

Product 1

HCID 57989347Methyl 2-isopropyl-5-methylthiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-bromo-2-oxobutanoate (4.6 g) and 2-methylpropanethioamide (2.5 g) in THF (100 mL) was heated at reflux for 18 hours. The solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution and the organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The residue was purified by flash silica chromatography using 17% ethyl acetate in isohexane as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 1.7 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure
  8. customThe residue was purified by flash silica chromatography
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-234bb86c22ec4e739794b4a40c27ecc8
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…