Potassium Carbonate → Thiazole, 2-[(3,4,4-trifluoro-3-butenyl)thio]-

HRID 1582176Notes

Reaction equation

HRID 1582176 reaction equation
[SH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:13]([C:16]([F:20])=[C:17]([F:19])[F:18])[CH2:14]Br>C(#N)C>[F:20][C:16](=[C:17]([F:19])[F:18])[CH2:13][CH2:14][S:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527881HCID 178527881, compound

Product 1

HCID 11447455Thiazole, 2-[(3,4,4-trifluoro-3-butenyl)thio]-Yield 86.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Mercaptothiazole (5.18 g), potassium carbonate (6.72 g) and 4-bromo-1,1,2-trifluorobutene-1 (9.21 g) are refluxed in acetonitrile (60 ml) in the presence of argon gas for 6 hours by heating. After the reaction mixture has reached room temperature, it is filtered and the solvent is distilled off. The residue is dissolved in dichloromethane and washed with 5% aqueous solution of sodium hydroxide and water in this order. It is dried over unhydrous sodium sulfate and purified by column chromatography (eluent: dichloromethane) to obtain 2-(3,4,4-trifluoro-3-butenyl-thio)thiazole (8.6 g) as pale yellow liquid (n20D 1.5200).

Workup

  1. temperatureby heating
  2. customhas reached room temperature
  3. filtrationit is filtered
  4. distillationthe solvent is distilled off
  5. dissolutionThe residue is dissolved in dichloromethane
  6. washwashed with 5% aqueous solution of sodium hydroxide and water in this order
  7. dry with materialIt is dried over unhydrous sodium sulfate
  8. custompurified by column chromatography (eluent: dichloromethane)

Sources & evidence

ORD record
ord-e2b8f333808345b8859dc34c25388125
Source dataset
uspto-grants-2004_05
Patent number
US06734198B1

Reaction notes

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