Ethanol → 2-[4-Chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrile

HRID 2414252Notes

Reaction equation

HRID 2414252 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:15]=[CH:14][C:13]([CH2:16][C:17]#[N:18])=[CH:12][C:5]=1[CH2:6][NH:7][C:8](=[O:11])[O:9][CH3:10].C(O)C.[N:22](OC(C)(C)C)=[O:23]>C(OCC)(=O)C.O>[Cl:3][C:4]1[CH:15]=[CH:14][C:13]([C:16](=[N:22][OH:23])[C:17]#[N:18])=[CH:12][C:5]=1[CH2:6][NH:7][C:8]([O:9][CH3:10])=[O:11]

Participants

7

Reactant 4

HCID 702EthanolHCID 10906Tert-Butyl nitriteHCID 14798Sodium HydroxideHCID 12151315methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate

Product 1

HCID 867595492-[4-Chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrileYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.15 g of sodium hydroxide and 0.60 g of methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate were added to 5 ml of ethanol, and 0.40 g of t-butyl nitrite was added to the mixture at room temperature, followed by stirring for 72 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=3/1) to obtain 0.46 g of 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-hydroxyiminoacetonitrile as a colorless viscous liquid.

Workup

  1. additionwas added to the mixture at room temperature
  2. customAfter completion of the reaction
  3. washby washing with water
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (Wakogel C-200, eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-cb6ec502b151473eb5758018af9d8739
Source dataset
uspto-grants-2004_11
Patent number
US06812229B1

Reaction notes

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