Ethanol → methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate

HRID 70235Notes

Reaction equation

HRID 70235 reaction equation
CC[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13](=O)[CH3:14])[CH:10]=[CH:9][C:8]=1[Cl:16])=[O:4].[NH2:17][OH:18].[CH2:19]([OH:21])C>>[Cl:16][C:8]1[CH:9]=[CH:10][C:11]([C:13](=[N:17][OH:18])[CH3:14])=[CH:12][C:7]=1[CH2:6][NH:5][C:3](=[O:4])[O:21][CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 787HydroxylamineHCID 66789789HCID 66789789, compound

Product 1

HCID 86641517methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate

Procedure

To a solution of methyl N-[(5-acetyl-2-chlorophenyl)methyl]acetamide (0.5 g, 2.1 mmol) (prepared according the method given in European Patent Publication EP 1586552) in ethanol (10 mL) was added an aqueous solution hydroxylamine (50% by wt) (0.82 g, 12.4 mmol). The reaction mixture was heated at refluxed overnight, and then concentrated to provide methyl N-[[2-chloro-5-[1-(hydroxyimino)ethyl]phenyl]methyl]carbamate as a white solid, which was used without purification. To N,N-dimethylformamide (5.0 mL) was added methyl N-[[2-chloro-5-[1-(hydroxyimino)ethyl]phenyl]methyl]carbamate (0.28 g, 1.1 mmol), 3-(chloropropyl)trimethylsilane (0.33 g, 2.2 mmol) and potassium carbonate (0.45 g, 3.3 mmol). This reaction mixture was then heated at 100° C. overnight, and then concentrated under reduced pressure. The resulting oil was purified by medium pressure liquid chromatography (0 to 100% gradient of ethyl acetate in hexanes as eluant) to yield the title compound, a compound of the present invention, as a clear oil. (0.22 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat refluxed overnight
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-65093298f851414c993ce38476c17eec
Source dataset
uspto-grants-2014_09
Patent number
US08822521B2

Reaction notes

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