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

HRID 375394Notes

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.C(=O)([O-])[O-:31].[Na+].[Na+]>C1(C)C=CC=CC=1>[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:31]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.29 g, 5.0 mmol) and piperazine (0.52 g, 6.0 mmol) in toluene (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 80° C. for 48 hours. After cooling to an ambient temperature, the reaction mixture was poured into saturated aqueous sodium carbonate solution, and extracted with toluene. The toluene 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 (1.29 g, 3.8 mmol, yield 77% ).

Workup

customto flow intothe flask
temperatureAfter cooling to an ambient temperature
extractionextracted with toluene
washThe toluene layer was washed with water
dry with materialbrine, and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-eecaf161e47f48ac897a9ede6fbd35a2
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484933

Reaction notes

Loading…