Trifluoroacetic anhydride → 5-Fluoro-3-(thiazol-2-ylcarbonyl)thiophenol

HRID 741811Notes

Reaction equation

HRID 741811 reaction equation
C[S:2]([C:4]1[CH:5]=[C:6]([C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:12])[CH:7]=[C:8]([F:10])[CH:9]=1)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClC(Cl)C>[F:10][C:8]1[CH:7]=[C:6]([C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[O:12])[CH:5]=[C:4]([SH:2])[CH:9]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 19426964HCID 19426964, compound

Product 1

HCID 194270015-Fluoro-3-(thiazol-2-ylcarbonyl)thiophenol

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the sulfoxide from Step 2 (0.35 g, 1.29 mmol) in dichloroethane (2.6 mL) was added TFAA (2.6 mL). The mixture was stirred at 80° C. for 0.5 h, cooled and evaporated. The residue was dissolved in MeOH: Et3N (1:1, 5 mL). The solvent was evaporated and taken up again in MeOH/Et3N. After evaporation of the solvent and chromatography using hexane:EtOAc (70:30) 0.28 g of the title compound was obtained.

Workup

  1. temperaturecooled
  2. customevaporated
  3. dissolutionThe residue was dissolved in MeOH: Et3N (1:1, 5 mL)
  4. customThe solvent was evaporated
  5. customAfter evaporation of the solvent and chromatography
  6. customwas obtained

Sources & evidence

ORD record
ord-52de2a1100364692b9a794d2ae57b248
Source dataset
uspto-grants-1996_09
Patent number
US05552437

Reaction notes

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