Dimethylamine → 2,6-dimethoxy-N,N-dimethylbenzamide

HRID 643877Notes

Reaction equation

HRID 643877 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:7]=1[C:8](Cl)=[O:9].CCOC(C)=O>C1COCC1>[CH3:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:7]=1[C:8]([N:2]([CH3:3])[CH3:1])=[O:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 748102,6-Dimethoxybenzoyl chloride

Product 1

HCID 32670112,6-dimethoxy-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethylamine (42 mL, 84 mmol) in THF at 0° C. is added 2,6-dimethoxybenzoyl chloride (5.58 g, 27.8 mmol) and it is warmed to RT and stirred for 18 h. The mixture is poured to EtOAc, washed with water, 1 N HCl solution and brine. The solvent is removed and concentrated to give the title compound and it is used in the next step.

Workup

  1. washwashed with water, 1 N HCl solution and brine
  2. customThe solvent is removed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-166453f5e1d247bebbc56a9bc45fa0f2
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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