Water → methyl N-{2-methyl-5-[1-(6-methylpyridin-2-yl methoxy)iminoethyl]benzyl}carbamate

HRID 2414258Notes

Reaction equation

[CH3:1][C:2]1[CH:13]=[CH:12][C:11]([C:14](=[N:16][OH:17])[CH3:15])=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8].[C:18](=O)([O-])[O-].[K+].[K+].Cl.Cl[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:13]=[CH:12][C:11]([C:14](=[N:16][O:17][CH2:18][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=2)[CH3:15])=[CH:10][C:3]=1[CH2:4][NH:5][C:6](=[O:9])[O:7][CH3:8]

Participants

Conditions

Temperature: 95 °C

Procedure

0.43 g of methyl N-[2-methyl-5-(1-hydroxyiminoethyl)benzyl]carbamate was dissolved in 15 ml of N,N-dimethylformamide, 0.75 g of potassium carbonate and 0.32 g of 2-chloro-6-methylpyridine hydrochloride were added thereto, followed by stirring under heating at from 90 to 100° C. for 8 hours. After completion of the reaction, the reaction solution was poured into water, extraction with ethyl acetate was carried out, followed by washing with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=4/1) to obtain 0.30 g of methyl N-{2-methyl-5-[1-(6-methylpyridin-2-yl methoxy)iminoethyl]benzyl}carbamate (m.p. 72-75° C.) as pale yellow crystals.

Workup

customAfter completion of the reaction
washby washing with water
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-ccc1da4f5fa746c5ae7eefbdecf7dae5
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812229B1

Reaction notes

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