4-Chlorobenzoyl chloride → 4-Chloro-N-methoxy-N-methylbenzamide

HRID 843760Notes

Reaction equation

HRID 843760 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1>[OH-].[Na+].ClCCl>[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([N:4]([CH3:5])[O:3][CH3:2])=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 112756634-Chloro-N-methoxy-N-methylbenzamideYield 131.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 11.38 gm (116.7 mMol) N-methoxy-N-methyl amine hydrochloride in 700 mL 1N sodium hydroxide was added a solution of 18.56 gm (106.04 mMol) 4-chlorobenzoyl chloride in 200 mL dichloromethane and the mixture was stirred at ambient. After 18 hours the phases were separated and the remaining aqueous was extracted well with dichloromethane. All organic phases were combined, dried over sodium sulfate and concentrated under reduced pressure to give 27.9 gm (95%) of the title compound as a clear oil.

Workup

  1. customAfter 18 hours the phases were separated
  2. extractionthe remaining aqueous was extracted well with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-91b56e0e362c469a99cdfa5b5fef71bb
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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