Dimethylformamide → 2-(5-Acetyl-ethoxybenzamido)-3-methylbenzamide

HRID 374787Notes

Reaction equation

HRID 374787 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH3:21])=[C:14]([CH:18]=1)[C:15]([OH:17])=O)(=[O:9])[CH3:8].CN(C)C=O.[NH2:27][C:28]1[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31]>ClCCl.N1C=CC=CC=1>[C:7]([C:10]1[CH:11]=[CH:12][C:13]([O:19][CH2:20][CH3:21])=[C:14]([CH:18]=1)[C:15]([NH:27][C:28]1[C:36]([CH3:37])=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31])=[O:17])(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 142218072-Amino-3-methylbenzamideHCID 185365885-Acetyl-2-ethoxybenzoic acid

Product 1

HCID 185365822-(5-Acetyl-ethoxybenzamido)-3-methylbenzamideYield 436.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (3.66 g, 0.0288 mol) was added dropwise to a stirred solution of 5-acetyl-2-ethoxybenzoic acid (3 g, 0.00144 mol) and dimethylformamide (0.1 ml) in dichloromethane (15 ml). The mixture was stirred at room temperature for 3 hours, then the solvent evaporated under vacuum and the residue azeotroped with hexane (3×50 ml). The crude acyl chloride was dissolved in dichloromethane (20 ml) and the solution added dropwise to a stirred solution of 2-amino-3-methylbenzamide (2.16 g, 0.0144 mol) in pyridine (40 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for a further 18 hours. The solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (50 ml) and this solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml), then dried (Na2SO4) and evaporated under vacuum. Trituration of the residue with diethyl ether gave the title compound as a white solid (2.14 g, 44%), m.p. 214°-216° C. Found: C,66.81; H,5.98; N,8.16. C19H20N2O4 requires C,67.04; H,5.92; N,8.23%.

Workup

  1. customthe solvent evaporated under vacuum
  2. customthe residue azeotroped with hexane (3×50 ml)
  3. dissolutionThe crude acyl chloride was dissolved in dichloromethane (20 ml)
  4. temperatureto warm to room temperature
  5. stirringstirred for a further 18 hours
  6. customThe solvent was removed by evaporation under vacuum
  7. dissolutionthe residue dissolved in dichloromethane (50 ml)
  8. washthis solution then washed with saturated aqueous sodium carbonate solution (50 ml), 2N hydrochloric acid (50 ml) and brine (50 ml)
  9. dry with materialdried (Na2SO4)
  10. customevaporated under vacuum

Sources & evidence

ORD record
ord-2e1cfb9d4f74440199ae167b5fa618c9
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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