Cysteamine → 1,1,1-Trifluoro-3-(thiazolidin-2-ylidene)propan-2-one

HRID 1519022Notes

Reaction equation

HRID 1519022 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].[F:5][C:6]([F:16])([F:15])[C:7](=[O:14])[CH:8]=[C:9](SC)SC>C(O)C>[F:5][C:6]([F:16])([F:15])[C:7](=[O:14])[CH:8]=[C:9]1[NH:1][CH2:2][CH2:3][S:4]1

Participants

4

Reactant 2

HCID 6058CysteamineHCID 14127909HCID 14127909, compound

Product 1

HCID 704180281,1,1-Trifluoro-3-(thiazolidin-2-ylidene)propan-2-oneYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 36 mg (0.46 mmol) of 2-aminoethanethiol dissolved in 10 mL of ethanol was added to 100 mg (0.46 mmol) of 1,1,1-trifluoro-4,4-bis(methylthio)-3-buten-2-one obtained by the method described in Comparative Example 4, and the mixture was refluxed under heating for 6 hours, then stirred at room temperature for 13 hours. Following reaction completion, the ethanol was distilled off under reduced pressure, after which the condensate was dissolved in ethyl acetate and washed once with water. The washed product was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure, giving 73 mg (yield, 81%) of 1,1,1-trifluoro-3-(thiazolidin-2-ylidene)propan-2-one.

Workup

  1. customobtained by the method
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 6 hours
  4. customreaction completion
  5. distillationthe ethanol was distilled off under reduced pressure
  6. dissolutionafter which the condensate was dissolved in ethyl acetate
  7. washwashed once with water
  8. dry with materialThe washed product was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6a4dad7b3fee4424982155999803cfd9
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

Loading…