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

HRID 375389Notes

Reaction equation

HRID 375389 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.N1CCCCC1.[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 6228DimethylformamideHCID 8082PiperidineHCID 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 piperidine (0.64 g, 7.5 mmol) in N,N-dimethylformamide (10 ml) was reacted in a reaction flask with tetrafluoroethylene, which was made to flow into the flask (ca. 0.7 liter/hr), with vigorous stirring at 50° C. for 21 hours. After cooling to an ambient temperature, the reaction mixture was poured into ice-water, and extracted with diethyl ether. The diethyl ether layer was washed with water and then brine, and dried over 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%). Unreacted part of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.30 g) was recovered.

Workup

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

Sources & evidence

ORD record
ord-0626e4699c3e43a687451c50c6ee91f2
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

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