Water → 2,4-Dichloro-N-methoxy-N-methylbenzamide

HRID 605574Notes

Reaction equation

HRID 605574 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].C(N(CC)CC)C.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].O>C(Cl)Cl>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16]([N:4]([O:3][CH3:2])[CH3:5])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 118453452,4-Dichloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 32.6 g of N-methoxymethanamine hydrochloride and 91.2 ml of triethylamine in 500 ml of DCM is cooled in an ice bath, and then 47 ml of 2,4-dichlorobenzoyl chloride are added slowly and the mixture is left to stir while allowing the temperature to rise to AT. After stirring for 1 hour at AT, water is added to the reaction mixture, the mixture is extracted with DCM, the organic phase is dried over Na2SO4 and the solvent is evaporated under vacuum. 53 g of the expected compound are obtained.

Workup

  1. temperatureis cooled in an ice bath
  2. waitthe mixture is left
  3. additionis added to the reaction mixture
  4. extractionthe mixture is extracted with DCM
  5. dry with materialthe organic phase is dried over Na2SO4
  6. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-848fe4355e8c472db559bd1b7fe9dfa8
Source dataset
uspto-grants-2011_03
Patent number
US07915258B2

Reaction notes

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