Dimethylformamide → Ethyl 4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate

HRID 270143Notes

Reaction equation

HRID 270143 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].CN(C=[O:27])C>FC(F)(F)C([O-])=O.[Ag+]>[OH:27][CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 179517684-Bromomethyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic Acid Ethyl Ester

Product 1

HCID 17951856Ethyl 4-(hydroxymethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 76299Silver trifluoroacetateCatalyst

Procedure

To a stirred solution of ethyl 4-(bromomethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazole-5-carboxylate (50g, 0.127moles, 1eq) in dry DMF (300ml) under a positive N2flow was added silver trifluoroacetate (42.02g, 0.191moles, 1.5eq) all at once as a solid. This was stirred at room temperature for 3.5hrs. The reaction was partitioned between ethyl ether (1.5L) and water (500ml). The phases were separated and the organic phase washed twice with water (500ml). After separation of the phases, the organic fraction was dried with Na2SO4, filtered and concentrated in vacuo. The crude trifluoroacetate product was used without characterization. Ethanol (300ml) was added and the reaction was refluxed for 10hrs. After cooling to room temperature the ethanol was removed in vacuo to yield 42g (100%) of the title compound. The product was used without purification.

Workup

  1. customThe reaction was partitioned between ethyl ether (1.5L) and water (500ml)
  2. customThe phases were separated
  3. washthe organic phase washed twice with water (500ml)
  4. customAfter separation of the phases
  5. dry with materialthe organic fraction was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionEthanol (300ml) was added
  9. temperaturethe reaction was refluxed for 10hrs
  10. temperatureAfter cooling to room temperature the ethanol
  11. customwas removed in vacuo

Sources & evidence

ORD record
ord-158830b14c2946e8b27c5d5c66a5bc33
Source dataset
uspto-grants-2008_11
Patent number
US07449468B2

Reaction notes

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