2-Ethoxybenzoyl chloride → 2-(2-Ethoxybenzamido)-6-methylbenzamide

HRID 374780Notes

Reaction equation

HRID 374780 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([NH2:6])=[O:5].[CH2:12]([O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18])[CH3:13]>N1C=CC=CC=1>[CH2:12]([O:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([NH2:6])=[O:5])=[O:18])[CH3:13]

Participants

4

Reactant 2

HCID 30163972-Ethoxybenzoyl chlorideHCID 167824692-Amino-6-methylbenzamide

Product 1

HCID 185366002-(2-Ethoxybenzamido)-6-methylbenzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-amino-6-methylbenzamide (UK Patent Application No 1,276,359; 5.49 g, 0.0365 mol), 2-ethoxybenzoyl chloride (7.67 g, 0.0415 mol) and pyridine (100 ml) was stirred at room temperature for 20 hours. The solvent was then removed by evaporation under vacuum and the residue dissolved in dichloromethane (200 ml). The solution was washed with saturated aqueous sodium carbonate solution (200 ml) and the aqueous phase back-extracted with further dichloromethane (2×100 ml). The organic solutions were combined, washed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml), then dried (Na2SO4) and evaporated under vacuum to give the title compound, which recrystallized from ethyl acetate as a colorless solid (6.86 g, 63%), m.p. 166°-168° C. Found: C,68.28; H,5.97; N,9.42. C17H18N2O3 requires C;68.44; H,6.08; N,9.39%.

Workup

  1. customThe solvent was then removed by evaporation under vacuum
  2. dissolutionthe residue dissolved in dichloromethane (200 ml)
  3. washThe solution was washed with saturated aqueous sodium carbonate solution (200 ml)
  4. extractionthe aqueous phase back-extracted with further dichloromethane (2×100 ml)
  5. washwashed successively with 2N hydrochloric acid (3×100 ml) and brine (100 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-891356be25e64e23bb37fbbfcfe2db44
Source dataset
uspto-grants-1996_01
Patent number
US05482941

Reaction notes

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