Triethylamine → 4-Chloro-N-methoxy-N-methylbenzamide

HRID 605575Notes

Reaction equation

HRID 605575 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(CC)CC)C.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([N:4]([O:3][CH3:2])[CH3:5])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85014-Chlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 112756634-Chloro-N-methoxy-N-methylbenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

31.2 g of N-methoxymethanamine hydrochloride and 91.2 ml of triethylamine in 500 ml of DCM is cooled in an ice bath, and then 56 g of 4-chlorobenzoyl chloride are added slowly and the mixture is left to stir at AT for 4 hours. A mixture of ice/water is added, 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. 60 g of the expected compound are obtained.

Workup

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

Sources & evidence

ORD record
ord-3a8342e2eefc48f1b9e95944b866347b
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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