N,N-Diethylaniline → HCID 18408347, compound

HRID 1385928Notes

Reaction equation

[CH2:1](N(CC)C1C=CC=CC=1)C.[Cl:12][C:13]1[C:18]([O:19][CH2:20][C:21]#C)=[CH:17][C:16]([C:23]2[C:24](=[O:34])[CH:25]=[C:26]([C:30]([F:33])([F:32])[F:31])[N:27]([CH3:29])[CH:28]=2)=[C:15]([F:35])[CH:14]=1.[F-].[Cs+]>O>[Cl:12][C:13]1[C:18]2[O:19][C:20]([CH3:21])=[CH:1][C:17]=2[C:16]([C:23]2[C:24](=[O:34])[CH:25]=[C:26]([C:30]([F:31])([F:33])[F:32])[N:27]([CH3:29])[CH:28]=2)=[C:15]([F:35])[CH:14]=1

Participants

Conditions

Temperature: 190 °C

Procedure

To 50 ml of N,N-diethylaniline, 0.64 g (1.8 mmol) of 5-(4-chloro-2-fluoro-5-propargyloxyphenyl)-1-methyl-2-trifluoromethyl-4(1H)-pyridone and 0.56 g (3.7 mmol) of cesium fluoride were added, and the mixture was stirred at from 180 to 200° C. for 2.5 hours This reaction solution was poured into water and extracted with ethyl acetate. After washing with concentrated hydrochloric acid, water and an aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and then, the obtained residue was purified by silica gel column chromatography to obtain 0.50 g (yield: 75%) of the desired product. Melting point: 208-211° C. 1H-NMR (400 MHz, CDCl3) δ value: 2.46(3H,s), 3.80(3H,s), 6.31(1H,s), 7.01(1H,s), 7.07(1H,d), 7.57(1H,d)ppm.

Workup

extractionextracted with ethyl acetate
washAfter washing with concentrated hydrochloric acid, water
dry with materialan aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous magnesium sulfate
distillationEthyl acetate was distilled off under reduced pressure
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cd1d4afdd95b4c3da6e7a4b651167008
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265349B1

Reaction notes

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