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

HRID 660609Notes

Reaction equation

HRID 660609 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].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 962WaterHCID 748102,6-Dimethoxybenzoyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of dimethylamine (2M in THF, 3 mL) and THF (2 mL) is added 2,6-dimethoxybenzoyl chloride (200.6 mg, 1 mmol) in THF (2 mL) dropwise. After the addition, the solution is stirred at RT for 1 h. Water is added and the suspension is extracted with EtOAc. The organic layer is washed with water and brine, and dried over sodium sulfate. The solvent is removed under reduced pressure to afford the title compound: 1H NMR (CDCl3) δ 7.26-7.22 (t, J=8.34 Hz, 1H), 6.56-6.53 (d, J=8.33 Hz, 2H), 3.79 (s, 6H), 3.12 (s, 3H), 2.82 (s, 3H).

Workup

  1. additionAfter the addition
  2. extractionthe suspension is extracted with EtOAc
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-a5e9b27bab7b4180a0b172bfa982e458
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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