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

HRID 1977617Notes

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-519cce04a6ca48c59a1e8c7f011767d2
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235743B1

Reaction notes

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