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

HRID 605576Notes

Reaction equation

HRID 605576 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][O:13][NH:14][CH3:15].C(N(CC)CC)C.O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([N:14]([O:13][CH3:12])[CH3:15])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 181853702-Chloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 ml of 2-chlorobenzoyl chloride are added slowly to a mixture of 37.33 g of N-methoxymethanamine hydrochloride and 104 ml of triethylamine in 500 ml of DCM and the mixture is left to stir overnight at AT. Water is added to the reaction mixture, the mixture is extracted with DCM, the organic phase is washed with a buffer solution pH=2 and dried over Na2SO4, and the solvent is evaporated off under vacuum. 78.57 g of the expected compound are obtained.

Workup

  1. waitthe mixture is left
  2. extractionthe mixture is extracted with DCM
  3. washthe organic phase is washed with a buffer solution pH=2
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-a2d3bd84d52348c9bdfe9e1ff8be64cf
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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