Phenylacetyl chloride → N-Hydroxy-N-methyl-2-phenylacetamide

HRID 2358013Notes

Reaction equation

HRID 2358013 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:12][NH:13][OH:14].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[OH:14][N:13]([CH3:12])[C:8](=[O:9])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 194437N-Hydroxy-N-methyl-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C. phenyl-acetyl chloride (11.2 mL) is added drop wise to a solution of N-methyl-hydroxylamine hydrochloride (7.07 g) and triethylamine (59 mL) in DCM (300 mL). After stirring for 90 min a sat. aqueous NaHCO3 solution is added, the layers are separated and the aqueous layer is extracted twice with DCM (2×200 mL). The solvents are removed in vacuo and the residue is purified by flash chromatography (EA/heptane 1/1) to give the desired N-hydroxy-acetamide as a colorless liquid.

Workup

  1. additionis added
  2. customthe layers are separated
  3. extractionthe aqueous layer is extracted twice with DCM (2×200 mL)
  4. customThe solvents are removed in vacuo
  5. customthe residue is purified by flash chromatography (EA/heptane 1/1)

Sources & evidence

ORD record
ord-08cbd3e0cce74e4fa4cf8a5a84813b72
Source dataset
uspto-grants-2010_07
Patent number
US07763638B2

Reaction notes

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