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

HRID 375395Notes

Reaction equation

Cl.[NH:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1.N1CC[O:22]CC1.[F:25][C:26]([F:30])=[C:27](F)F.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:25][CH:26]([F:30])[C:27]([N:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1)=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (1.47 g, 5.0 mmol) and morpholine (1.57 g, 18.0 mmol) in N,N-dimethylformamide (10 ml) charged in a reaction flask was reacted with tetrafluoroethylene, which was made to flow intothe flask (ca. 0.7 liter/hr), with vigorous stirring at 60° C. for 2 hours. After cooling to an ambient temperature, the reaction mixture was poured into 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 (70 ml) and then brine (70 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 (1.47 g, 4.4 mmol, yield 87%).

Workup

customto flow intothe flask
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 (70 ml)
dry with materialbrine (70 ml), and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off

Sources & evidence

ORD record: ord-d7dcdc96c83a4b3abad24f5941865b01
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484933

Reaction notes

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