Water → 2-Chloro-N-methoxy-N-methylbenzamide

HRID 1027684Notes

Reaction equation

HRID 1027684 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[CH3:12][NH:13][O:14][CH3:15].N1C=CC=CC=1.O>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:13]([O:14][CH3:15])[CH3:12])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 691102-Chlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 181853702-Chloro-N-methoxy-N-methylbenzamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chlorobenzoyl chloride (8 g, 46 mmol) in dichloromethane (200 mL) at 0° C. was added N,O-dimethylhydroxylamine hydrochloride (4.9 g, 50 mmol) followed by pyridine (11 mL, 137 mmol). The mixture was stirred at room temperature for 16 hours. Water was added to the reaction mixture and organic layer was washed with brine, dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel gave 2-chloro-N-methoxy-N-methylbenzamide (21) (7.8 g, 39.2 mmol, 85%) as clear oil.

Workup

  1. washwas washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customPurification by chromatography on silica gel

Sources & evidence

ORD record
ord-b72fea5e90fd4ee0b7a6e5bfe9b98fa0
Source dataset
uspto-grants-2014_05
Patent number
US08735399B2

Reaction notes

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