Methyl iodide → 2-[4-Chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-methoxyiminoacetonitrile
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:11][OH:12])[C:9]#[N:10])=[CH:4][C:3]=1[CH2:13][NH:14][C:15]([O:17][CH3:18])=[O:16].[CH3:19]I>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[N:11][O:12][CH3:19])[C:9]#[N:10])=[CH:4][C:3]=1[CH2:13][NH:14][C:15]([O:17][CH3:18])=[O:16]Participants
Procedure
0.36 g of 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrile and 0.54 g of a 28% sodium methylate methanol solution were added to 5 ml of methanol, and 0.49 g of methyl iodide was added thereto, followed by stirring at room temperature for 24 hours. The reaction solution was vacuum concentrated, the solvent was distilled off, water was added to the residue, extraction with ethyl acetate was carried out, 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=4/1-5/1) to obtain 0.18 g of 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-methoxyiminoacetonitrile as colorless crystals (m.p. 104-107° C.)
Workup
- additionwas added
- concentrationconcentrated
- distillationthe solvent was distilled off
- additionwater was added to the residue, extraction with ethyl acetate
- 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=4/1-5/1)
Sources & evidence
- ORD record
- ord-1707d261c467416fb1b0d704048b667a
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06812229B1
Reaction notes
Loading…