Dimethylamine → N,N,3-trimethyl-4-nitrobenzamide

HRID 562507

Reaction equation

HRID 562507 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].C(C1NC=CN=1)([C:16]1[NH:17][CH:18]=CN=1)=O.CNC>CN(C=O)C>[CH3:16][N:17]([CH3:18])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[CH:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 183703-Methyl-4-nitrobenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 786992N,N,3-trimethyl-4-nitrobenzamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methyl-4-nitrobenzoic acid (3.0 g, 16.56 mmol) in DMF (30 mL) was stirred with carbonyl diimidazole (3.22 g, 1.2 Eq.) for 90 mins. The reaction mixture was cooled in an icebath, and dimethylamine (2 M in THF, 25 mL, 3 Eq.) was added. The mixture was then allowed to warm to room temperature and stirred for 2 hours. The mixture was poured onto ice water (200 ml) and extracted with EtOAc (×6). The combined extracts were washed with brine, dried over MgSO4, filtered and evaporated. Tritration with ether followed by filtration gave N,N,3-trimethyl-4-nitrobenzamide (2.6 g, colourless solid); MS (ES+) 209.

Workup

  1. additionwas added
  2. additionThe mixture was poured onto ice water (200 ml)
  3. extractionextracted with EtOAc (×6)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. filtrationTritration with ether followed by filtration

Sources & evidence

ORD record
ord-71d20b4c1b904e69a4bb652094874409
Source dataset
uspto-grants-2011_11
Patent number
US08067417B2

Linked notes

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