Dimethylamine → N,N-dimethyl-2-nitrobenzamide

HRID 2294139Notes

Reaction equation

HRID 2294139 reaction equation
[CH3:1][NH:2][CH3:3].[OH-].[Na+].[N+:6]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](Cl)=[O:12])([O-:8])=[O:7]>O1CCOCC1>[CH3:1][N:2]([CH3:3])[C:11](=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[N+:6]([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 118752-Nitrobenzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 3261775N,N-dimethyl-2-nitrobenzamideYield 57.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of dimethylamine (30 g, 270 mmol) and sodium hydroxide (7.2 g, 180 mmol) in 60 mL of dioxane was stirred and 2-nitrobenzoyl chloride (23.8 mL, 180 mmol) in 100 mL of dioxane was added dropwise. The mixture was stirred at room temperature for approximately 12 hours and then partitioned between 100 mL of saturated sodium bicarbonate solution and 150 mL of ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×100 mL) and the combined ethyl acetate was washed with brine, dried (Na2SO4) and concentrated. The residue was purified on silica gel by flash chromatography eluting with 4% methanol/methylene chloride to give N,N-dimethyl-2-nitrobenzamide (20 g, 103 mmol), m.p. 74°-76° C.

Workup

  1. stirringThe mixture was stirred at room temperature for approximately 12 hours
  2. custompartitioned between 100 mL of saturated sodium bicarbonate solution and 150 mL of ethyl acetate
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
  4. washthe combined ethyl acetate was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel by flash chromatography
  8. washeluting with 4% methanol/methylene chloride

Sources & evidence

ORD record
ord-fed0dc3ce6d84218809fe4321f896155
Source dataset
uspto-grants-1997_11
Patent number
US05688795

Reaction notes

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