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

HRID 1766110Notes

Reaction equation

HRID 1766110 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 (50 g, 0.127 moles, 1 eq) in dry DMF (300 ml) under a positive N2 flow was added silver trifluoroacetate (42.02 g, 0.191 moles, 1.5 eq) all at once as a solid. This was stirred at room temperature for 3.5 hrs. The reaction was partitioned between ethyl ether (1.5 L) and water (500 ml). The phases were separated and the organic phase was washed twice with water (500 ml). 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 (300 ml) was added and the reaction was refluxed for 10 hrs. After cooling to room temperature the ethanol was removed in vacuo to yield 42 g (100%) of the title compound. The product was used without purification.

Workup

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

Sources & evidence

ORD record
ord-9627adc436a54bdabf1b688188526db1
Source dataset
uspto-grants-2007_06
Patent number
US07229998B2

Reaction notes

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