Thioacetamide → HCID 23560696, compound

HRID 1058346Notes

Reaction equation

HRID 1058346 reaction equation
Cl[C:2]([CH3:12])([CH3:11])[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.[C:13]([NH2:16])(=[S:15])[CH3:14]>C(O)C>[CH2:9]([O:8][C:6]([C:5]1[S:15][C:13]([CH3:14])=[N:16][C:3]=1[CH:2]([CH3:12])[CH3:11])=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 18673018HCID 18673018, compound

Product 1

HCID 23560696HCID 23560696, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-chloroisobutyrylacetate from step A (1.58 g, 8.2 mmol, ˜66% pure) in ethanol (20 mL) at 25° C. was added thioacetamide (617 mg, 8.2 mmol) and the reaction mixture was stirred at reflux for 24 h. After the solvents were removed under reduced pressure, the residual oil was diluted with ethyl acetate (100 mL), washed in turn with water (75 mL) and brine (75 mL), then was dried (MgSO4), filtered and concentrated in vacuo. The residue was flash chromatographed over silica gel (5% diethyl ether in hexanes) to yield 4-(1-methylethyl)-2-methylthiazole-5-carboxylic acid ethyl ester (1.1 g, 63% yield) as a yellow oil.

Workup

  1. temperatureat reflux for 24 h
  2. customAfter the solvents were removed under reduced pressure
  3. additionthe residual oil was diluted with ethyl acetate (100 mL)
  4. washwashed in turn with water (75 mL) and brine (75 mL)
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customchromatographed over silica gel (5% diethyl ether in hexanes)

Sources & evidence

ORD record
ord-7d84de8db7bc4f768fa227d1422922a1
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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