Methylamine → N,3,5-Trimethyl-4-nitrobenzamide

HRID 237518Notes

Reaction equation

HRID 237518 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:26])[C:22]=1[N+:23]([O-:25])=[O:24])[C:17](O)=[O:18].CN>O1CCCC1>[CH3:1][NH:3][C:17](=[O:18])[C:16]1[CH:15]=[C:14]([CH3:13])[C:22]([N+:23]([O-:25])=[O:24])=[C:21]([CH3:26])[CH:20]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 86697180N,3,5-Trimethyl-4-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (914 mg) is added to a suspension of 3,5-dimethyl-4-nitrobenzoic acid (1 g) in tetrahydrofuran (10 mL). The mixture is stirred for 3 hours at room temperature, methylamine (7.7 mL, 2 M in tetrahydrofuran) is added and the mixture is stirred for further 30 minutes. After concentration the mixture is diluted with ethyl acetate and washed with hydrochloric acid (0.2 M), saturated aqueous NaHCO3 solution and brine. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 1 g; LC (method 20): tR=4.82 min; Mass spectrum (ESI+): m/z=209 [M+H]+.

Workup

  1. stirringthe mixture is stirred for further 30 minutes
  2. concentrationAfter concentration the mixture
  3. additionis diluted with ethyl acetate
  4. washwashed with hydrochloric acid (0.2 M), saturated aqueous NaHCO3 solution and brine
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e528b9000b804ca2ac24941ed8680a12
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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