2-Ethoxybenzoyl chloride → 2-(Ethoxybenzamido)-3-methoxybenzamide

HRID 412033Notes

Reaction equation

HRID 412033 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])[CH3:2].[NH2:13][C:14]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17]>N1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:13][C:14]1[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 30163972-Ethoxybenzoyl chlorideHCID 185365712-Amino-3-methoxybenzamide

Product 1

HCID 185365662-(Ethoxybenzamido)-3-methoxybenzamideYield 54.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Ethoxybenzoyl chloride (8.9 g, 0.048 mol) was added dropwise to a stirred solution of 2-amino-3-methoxybenzamide (4.0 g, 0.024 mol) in pyridine (35 ml) under a nitrogen atmosphere at 0° C. After 20 hours at room temperature, the solvent was removed by evaporation under vacuum, the residue dissolved in dichloromethane (100 ml) and the solution washed successively with 2N hydrochloric acid (2×100 ml) and saturated aqueous sodium hydrogen carbonate solution (2×100 ml). The organic phase was dried (MgSO4) and evaporated under vacuum, then the resulting oil chromatographed on silica gel (40 g), eluting with a mixture of methanol in-dichloromethane (2%), to give the title compound as a colourless solid (4.1 g, 54%), m.p. 177-179° C.

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. dissolutionthe residue dissolved in dichloromethane (100 ml)
  3. washthe solution washed successively with 2N hydrochloric acid (2×100 ml) and saturated aqueous sodium hydrogen carbonate solution (2×100 ml)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated under vacuum
  6. customthe resulting oil chromatographed on silica gel (40 g)
  7. washeluting with a mixture of methanol in-dichloromethane (2%)

Sources & evidence

ORD record
ord-588c7520f5b14ee59b32827024981d1c
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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