3-Bromo-1,1,1-trifluoro-2-propanone → Ethyl 4-(trifluoromethyl)thiazole-2-carboxylate

HRID 1497398Notes

Reaction equation

HRID 1497398 reaction equation
[NH2:1][C:2](=[S:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].Br[CH2:10][C:11](=O)[C:12]([F:15])([F:14])[F:13]>C(O)C>[F:13][C:12]([F:15])([F:14])[C:11]1[N:1]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:8][CH:10]=1

Participants

4

Reactant 2

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 2733398Ethyl thiooxamate

Product 1

HCID 23560697Ethyl 4-(trifluoromethyl)thiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl amino(thioxo)acetate (4 g) and 3-bromo-1,1,1-trifluoroacetone (3.1 ml) in ethanol (150 ml) was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate) to give the title compound (3.56 g).

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-952f4d1a092b4325a976f92b6c14a45f
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

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