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

HRID 375392Notes

Reaction equation

HRID 375392 reaction equation
Cl.[NH:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1.N1CCNCC1.C(N(CC)CC)C.[F:32][C:33]([F:37])=[C:34](F)F.C[O:39]CCOCCOC>>[F:32][CH:33]([F:37])[C:34]([N:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1)=[O:39]

Participants

6

Reactant 5

HCID 4837PiperazineHCID 8150DiglymeHCID 8301TetrafluoroethyleneHCID 8471TriethylamineHCID 214800712-Imino-3-(3-trifluoromethyl-phenyl)-5-methylthiazoline hydrochloride

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 60%

Conditions

Temperature
70 °C

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride salt (1.47 g, 5.0 mmol), piperazine (0.64 g, 7.5 mmol) and triethylamine (1.52 g, 15.0 mmol) in diglyme (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow intothe flask (ca. 0.7 liter/hr), with vigorous stirring at 70° C. for 24 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 (1.01 g, 3.0 mmol, yield 60%).

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-422c34cb68ba4bdcb5025b23531f5e03
Source dataset
uspto-grants-1996_01
Patent number
US05484933

Reaction notes

Loading…