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

HRID 600938Notes

Reaction equation

HRID 600938 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][NH:12][O:13][CH3:14].C(N(CC)CC)C.NC1C(N)=NC=CC=1>ClCCl>[CH3:14][O:13][N:12]([CH3:11])[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 99562,3-DiaminopyridineHCID 14232N,O-Dimethylhydroxylamine

Product 1

HCID 10419762N-Methoxy-N-methyl-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenylacetyl chloride (commercially available, 4.7 g, 30.5 mmol) in dichloromethane (100 ml) was treated with N,O dimethylhydroxylamine (3.25 g, 33.5 mmol), followed by the addition of triethyl amine (8.5. g 61 mmol) and diaminopyridine (305 mgs). The mixture was stirred at room temperature overnight. The mixture was quenched with water (50 mL) and a saturated solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by MPLC with 0 to 2% MeOH:CH2Cl2 to give N-methoxy-N-methyl-2-phenylacetamide, (Intermediate 13) (3.5 g 78.7%).

Workup

  1. customThe mixture was quenched with water (50 mL)
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by MPLC with 0 to 2% MeOH

Sources & evidence

ORD record
ord-24a9cd2dc5c844acb348c25a7976dfe8
Source dataset
uspto-grants-2011_03
Patent number
US07902247B2

Reaction notes

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