Tetrafluoroethylene → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline
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.NCCN1CCNCC1.[F:27][C:28]([F:32])=[C:29](F)F.C(=O)([O-])[O-:34].[Na+].[Na+]>CN(C)C=O>[F:27][CH:28]([F:32])[C:29]([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
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (1.29 g, 5.0 mmol) and 1-(2-aminoethyl)piperazine (0.78 g, 6.0 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 33 hours. After cooling to an ambient temperature, the reaction mixture was poured into saturated aqueous sodium carbonate solution, 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 (1.18 g, 3.5 mmol, yield 70%). Unreacted part of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.12 g) was recovered.
Workup
- temperatureAfter cooling to an ambient temperature
- extractionextracted with diethyl ether
- washThe diethyl ether layer was washed with water
- dry with materialbrine, and dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-7a6ab38ecbab496ab43f0e31b0c5f382
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05484933
Reaction notes
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