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

HRID 843882Notes

Reaction equation

HRID 843882 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 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution 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 temperature. After 18 hours the phases were separated and the remaining aqueous was extracted well with dichloromethane. All organic phases are 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-e738f68b09cd404c9e37ca306a464857
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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