Dimethylamine → N,N-dimethyl-3-nitrobenzamide

HRID 581752Notes

Reaction equation

HRID 581752 reaction equation
[CH3:1][NH:2][CH3:3].[N+:4]([C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10](Cl)=[O:11])([O-:6])=[O:5].C(OCC)(=O)C>O1CCOCC1>[CH3:1][N:2]([CH3:3])[C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([N+:4]([O-:6])=[O:5])[CH:8]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 8857Ethyl Acetate

Product 1

HCID 347759N,N-dimethyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Dimethylamine (50% aqueous solution, 3.6 ml) was stirred in an ice bath and a solution of 3-nitrobenzoyl chloride (1.8 g) in 1,4-dioxan (4 ml) was dropwise added thereto. The resulting mixture was stirred vigorously at ambient temperature for 2.5 hours. Ethyl acetate was added and organic layer was washed with water, 1N hydrochloric acid, 1N sodium hydroxide, water and saturated sodium chloride solution successively and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was recrystallized from benzene-n-hexane to afford N,N-dimethyl-3-nitrobenzamide (1.5 g) as a pale yellow prism. mp: 84.7-87.7° C.

Workup

  1. washorganic layer was washed with water, 1N hydrochloric acid, 1N sodium hydroxide, water and saturated sodium chloride solution successively
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationAfter filtration and concentration
  4. customthe residue was recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-c4e6fd49983f422cb74d7bc4ec17f0a7
Source dataset
uspto-grants-1999_07
Patent number
US05922711

Reaction notes

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