N-(2-bromothiazol-4-yl)-2,2,2-trifluoroacetamide → 2,2,2-trifluoro-N-(thiazol-4-yl)acetamide

HRID 596409Notes

Reaction equation

HRID 596409 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([NH:7][C:8](=[O:13])[C:9]([F:12])([F:11])[F:10])[N:6]=1.O.O.O.C([O-])(=O)C.[Na+]>[Pd].C(O)C>[F:12][C:9]([F:10])([F:11])[C:8]([NH:7][C:5]1[N:6]=[CH:2][S:3][CH:4]=1)=[O:13]

Participants

5

Reactant 2

HCID 20377171N-(2-bromothiazol-4-yl)-2,2,2-trifluoroacetamideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 214496592,2,2-trifluoro-N-(thiazol-4-yl)acetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 50 g. (0.182 mole) of 2-bromo-4-trifluoroacetamidothiazole 36.5 g. (0.268 mole) of sodium acetate, trihydrate and 16.6 g. of 10% palladium on carbon in 1.5 l. of absolute ethanol is hydrogenated at 1 atmosphere over 18 hours at room temperature. The catalyst is filtered off and washed well with ethanol. The filtrate is evaporated to dryness and the residue extracted several times with warm methylene chloride. The combined extracts are evaporated to dryness and the residue crystallized from carbon tetrachloride (activated carbon treatment) to give 25 g. (70%) of heavy white crystals m.p. 138°-9° C. Recrystallization of the second crop obtained from the mother liquor raises the yield to 28.5 g. (80%). The product can also be satisfactorily recrystallized from ethanol/water mixtures.

Workup

  1. additionA mixture of 50 g
  2. filtrationThe catalyst is filtered off
  3. washwashed well with ethanol
  4. customThe filtrate is evaporated to dryness
  5. extractionthe residue extracted several times with warm methylene chloride
  6. customThe combined extracts are evaporated to dryness
  7. customthe residue crystallized from carbon tetrachloride (activated carbon treatment)
  8. customto give 25 g
  9. customRecrystallization of the second crop
  10. customobtained from the mother liquor
  11. temperatureraises the
  12. customyield to 28.5 g
  13. customThe product can also be satisfactorily recrystallized from ethanol/water mixtures

Sources & evidence

ORD record
ord-b9b393e094ff4159a896bef2597955b8
Source dataset
uspto-grants-1977_03
Patent number
US04011210

Reaction notes

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