4-Methylmorpholine → N,N-dimethyl-2-nitrobenzamide

HRID 1602792Notes

Reaction equation

HRID 1602792 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](O)=[O:7])([O-:3])=[O:2].[Cl-].[CH3:14][NH2+:15][CH3:16].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>ClCCl>[CH3:14][N:15]([CH3:16])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 110872-Nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12954980Dimethylazanium;chloride

Product 1

HCID 3261775N,N-dimethyl-2-nitrobenzamideYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 g 2-nitrobenzoic acid and 0.98 g dimethylammonium chloride in dichloromethane at 0° C. were added 2.29 g 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, 1.62 g N-hydroxy-benzotriazol and 6.05 g N-methyl-morpholine. The resulting mixture was stirred at room temperature overnight. The reaction mixture was then washed sequentially, with saturated sodium hydrogen carbonate, a 5% aqueous solution of citric acid and brine. The organic phase was dried over sodium sulfate. After filteration the solvent was removed in vacuo yielding N,N-dimethyl-2-nitrobenzamide (2.13 g).

Workup

  1. washThe reaction mixture was then washed sequentially, with saturated sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customAfter filteration the solvent was removed in vacuo

Sources & evidence

ORD record
ord-33c1a8cf5cd94fefac4b80ea38252523
Source dataset
uspto-grants-1999_11
Patent number
US05985837

Reaction notes

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