Dimethylformamide → 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.C(N)CCC.C(N(CC)CC)C.[F:30][C:31]([F:35])=[C:32](F)F.CN(C)C=[O:39]>>[F:30][CH:31]([F:35])[C:32]([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:39]Participants
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.52 g, 2.0 mmol), n-butylamine (0.44 g, 6.0 mmol) and triethylamine (0.6 1 g, 6.0 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 13 hours. After cooled to an ambient temperature, the reaction mixture was poured into ice-water, and extracted with diethyl ether. The ether layer was washed with 5% hydrochloric acid, 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 (0.50 g, 1.5 mmol, yield 74%).
Workup
- customto flow intothe flask
- temperatureAfter cooled to an ambient temperature
- extractionextracted with diethyl ether
- washThe ether layer was washed with 5% hydrochloric acid, water
- dry with materialbrine, and dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-27639613370e47a382672397998553e9
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05484933
Reaction notes
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