Potassium Fluoride → HCID 18408346, compound

HRID 1385958Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:13]=2Cl)=[CH:4][CH:3]=1.[F-:21].[K+]>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:13]=2[F:21])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To 10 ml of dimethylsulfoxide, 0.33 g (1.09 mmol) of 3-(4-chlorophenyl)-4-chloro-1-methyl-6-trifluoromethyl-2(1H)-pyridone and 0.05 g (0.86 mmol) of potassium fluoride were dissolved, followed by heating and stirring at 120° C. for 2 hours. After completion of the at reaction, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.12 g (yield: 38%) of the desired product. Melting point: 120-122° C. 1H-NMR (300 MHz, CDCl3) δ value: 3.42(3H,d), 6.20(1H,d), 7.16(2H,d), 7.40(2H,d)ppm.

Workup

temperatureby heating
customAfter completion of the at reaction
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
distillationThe organic layer was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0b84645b09ab43ae8c296b16d7a31f41
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265349B1

Reaction notes

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