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

HRID 39337

Reaction equation

HRID 39337 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-d3b48ac36ef04da0a64fbe747cc56d37
Source dataset
uspto-grants-2013_09
Patent number
US08524902B2

Linked notes

Loading…