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

HRID 375390Notes

Reaction equation

HRID 375390 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.CN(CCCN)C.[F:25][C:26]([F:30])=[C:27](F)F.CN(C)C=[O:34]>>[F:25][CH:26]([F:30])[C:27]([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:34]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8301TetrafluoroethyleneHCID 110215462(3H)-Thiazolimine, 5-methyl-3-[3-(trifluoromethyl)phenyl]-

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 35%

Conditions

Temperature
50 °C

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.29 g, 5.0 mmol) and 3-(N,N-dimethylamino)propylamine (0.77 g, 7.5 mmol) in N,N-dimethylformamide (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow intothe flask (ca. 0.3 liter/hr), with vigorous stirring at 50° C. for 17 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 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 (0.59 g, 1.8 mmol, yield 35%). Unreacted part of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.50 g) was recovered.

Workup

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

Sources & evidence

ORD record
ord-27ae909bfb244409870af5d5a050e108
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

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