Triethylamine → N,N-Dimethyl-4-nitro-benzamide

HRID 1874071Notes

Reaction equation

HRID 1874071 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:14][NH:15][CH3:16].C(N(CC)CC)C>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:15]([CH3:16])[CH3:14])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 138975N,N-Dimethyl-4-nitro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-nitrobenzoyl chloride (7.20 g, 38.8 mmol) and dimethylamine hydrochloride (3.20 g, 39.2 mmol) in 100 mL DCM is added triethyl amine (14.0 mL, 99.6 mmol) at 0° C. The cooling bath is removed and the reaction mixture is stirred overnight at RT. Then 300 mL DCM is added and the reaction mixture is washed with 50% saturated aqueous ammonium chloride, water, 50% saturated aqueous sodium hydrogen carbonate and 0.1 M aqueous NaOH. The organic phase is dried over MgSO4 and concentrated in vacuo. Yield: 5.37 g.

Workup

  1. customThe cooling bath is removed
  2. additionThen 300 mL DCM is added
  3. washthe reaction mixture is washed with 50% saturated aqueous ammonium chloride, water, 50% saturated aqueous sodium hydrogen carbonate and 0.1 M aqueous NaOH
  4. dry with materialThe organic phase is dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-972c4e6add9c40cf8e05aafeeba5f478
Source dataset
uspto-grants-2012_11
Patent number
US08304556B2

Reaction notes

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