O-Cresol → 2-[2-(5-fluoro-6-o-tolyloxy-pyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide

HRID 278377Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])=[N:6][CH:7]=[N:8][C:9]=1F.[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[OH:33]>CN(C)C=O>[F:3][C:4]1[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])=[N:6][CH:7]=[N:8][C:9]=1[O:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:26]

Participants

Conditions

Temperature: 25 °C

Procedure

With cooling, 0.25 g (0.0062 mol) of sodium hydride (60%) are added to a mixture of 2 g (0.0062 mol) of 2-[2-(5,6-difluoropyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide and 0.67 g (0.0062 mol) of 2-methylphenol in 20 ml of dimethylformamide, and the mixture is stirred at 25° C. for 12 hours. The reaction mixture is poured onto water and extracted with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is distilled off under reduced pressure. 1.5 g (58.9%) of 2-[2-(5-fluoro-6-o-tolyloxy-pyrimidin-4-yloxy)-phenyl]-2-methoxyimino-N-methyl-acetamide are obtained.

Workup

temperatureWith cooling
additionThe reaction mixture is poured onto water
extractionextracted with ethyl acetate
dry with materialthe organic phase is dried over sodium sulphate
distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record: ord-681c321d0e184ccc80730c38bd91f7c9
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359133B2

Reaction notes

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