Piperidine → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline

HRID 375397Notes

Reaction equation

HRID 375397 reaction equation
N1CCCCC1.[F:7][C:8]([F:12])=[C:9](F)F.Cl.[NH:14]=[C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH:18]=[C:17]([CH3:30])[S:16]1.C(=O)([O-])[OH:32].[Na+]>CN(C)C=O>[F:7][CH:8]([F:12])[C:9]([N:14]=[C:15]1[N:19]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=2)[CH:18]=[C:17]([CH3:30])[S:16]1)=[O:32]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8301TetrafluoroethyleneHCID 516892Sodium BicarbonateHCID 214800712-Imino-3-(3-trifluoromethyl-phenyl)-5-methylthiazoline hydrochloride

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of piperidine (0.57 g, 6.7 mmol) in N,N-dimethylformamide (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow into the flask (ca. 0.7 liter/hr), with vigorous stirring at 50° C. for 10 hours. After cooling to an ambient temperature, 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (1.29 g, 5.0 mmol) was added tothe reaction mixture and allowed to react overnight at room temperature and then at 50° C. for 8 hours. After cooling to an ambient temperature, the reaction solution was poured intoa saturated aqueous sodium hydrogencarbonate solution, and extracted twice with toluene (100 ml×2). The toluene layer was washed twice with 5% hydrochloric acid (50 ml×2) and water (50 ml) and then brine (50 ml), and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was subjected to silica gel column chromatography, which afforded 2-difluoroacetylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.83 g, 2.5 mmol, yield 49%).

Workup

  1. temperatureAfter cooling to an ambient temperature
  2. customtothe reaction mixture
  3. customto react overnight at room temperature
  4. waitat 50° C. for 8 hours
  5. temperatureAfter cooling to an ambient temperature
  6. extractionextracted twice with toluene (100 ml×2)
  7. washThe toluene layer was washed twice with 5% hydrochloric acid (50 ml×2) and water (50 ml)
  8. dry with materialbrine (50 ml), and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-92f86901ad5f460e9b290e6ef672e38d
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

Loading…