Morpholine → 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.N1CC[O:21]CC1.[F:24][C:25]([F:29])=[C:26](F)F.C(=O)([O-])O.[Na+]>CN(C)C=O>[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:21]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 morpholine (0.96 g, 11.0 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 13 hours. After cooling to an ambient temperature, the reaction mixture was poured into a saturated aqueous sodium hydrogencarbonate solution (100 ml), and extracted twice with toluene (100 ml×2). The toluene layer was washed twice with 5% hydrochloric acid (50 ml×2) and water (50 ml) and then brine (50 ml), 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 (1.64 g, 4.9 mmol, yield 98%).
Workup
- temperatureAfter cooling to an ambient temperature
- extractionextracted twice with toluene (100 ml×2)
- washThe toluene layer was washed twice with 5% hydrochloric acid (50 ml×2) and water (50 ml)
- dry with materialbrine (50 ml), and dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
Sources & evidence
- ORD record
- ord-54e67a2266b5454486e77d1eef3e31d4
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05484933
Reaction notes
Loading…