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

HRID 375391Notes

Reaction equation

HRID 375391 reaction equation
[NH:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH:5]=[C:4]([CH3:17])[S:3]1.N1CCNCC1.[F:24][C:25]([F:29])=[C:26](F)F.CN(C)C=[O:33]>>[F:24][CH:25]([F:29])[C:26]([N:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:14])[F:15])[CH:8]=2)[CH:5]=[C:4]([CH3:17])[S:3]1)=[O:33]

Participants

5

Reactant 4

HCID 4837PiperazineHCID 6228DimethylformamideHCID 8301TetrafluoroethyleneHCID 110215462(3H)-Thiazolimine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 74%

Conditions

Temperature
50 °C

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.29 g, 5.0 mmol) and piperazine (0.65 g, 7.5 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 9 hours. After cooling to an ambient temperature, the reaction mixture was poured into ice-water, and extracted with diethyl ether. The ether layer was washed with water and then brine, 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 (1.24 g, 3.7 mmol, yield 74%).

Workup

  1. temperatureAfter cooling to an ambient temperature
  2. extractionextracted with diethyl ether
  3. washThe ether layer was washed with water
  4. dry with materialbrine, and dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c18c9651add04e3983791ae6dc385ada
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

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