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(NCC)C.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 (0.77 g, 3.0 mmol), diethylamine (1.06 g, 14.5 mmol) and triethylamine (0.91 g, 9.0 mmol) in N,N-dimethylformamide (15 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow into the 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 ethyl acetate. The ethyl acetate 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 (eluent, n-hexane: ethyl acetate=2:1), which afforded 2-difluoroacetylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (0.82 g, 2.4 mmol, yield 81%).
Workup
- temperatureAfter cooling to an ambient temperature
- extractionextracted with ethyl acetate
- washThe ethyl acetate layer was washed with water
- dry with materialbrine, and dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-a8cec7462a0e498fae5a280336c00ccf
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05484933
Reaction notes
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