Potassium Carbonate → Benzamide

HRID 266404Notes

Reaction equation

HRID 266404 reaction equation
N[C:2]1[C:10](Cl)=[CH:9][C:5]([C:6](O)=[O:7])=[C:4](OC)[CH:3]=1.C1N=C[N:16](C(N2C=NC=C2)=O)C=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:6]([NH2:16])(=[O:7])[C:5]1[CH:9]=[CH:10][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 816264-Amino-5-chloro-2-methoxybenzoic acid

Product 1

HCID 2331Benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-amino-5-chloro-2-methoxybenzoic acid in freshly distilled DMF is added CDI (1 equivalent). After 1 hour at room temperature a solution of amine 35 (1 equivalent) in DMF is added. The reaction mixture is stirred at room temperature for 16 hours and concentrated in vacuo to give a residue which is treated with 15% potassium carbonate and extracted with chloroform (3×). The combined organic extracts are washed successively with water and brine and then dried over sodium sulfate. Concentration gives a solid which is purified on silica gel eluting with 7/93 MeOH(NH3)/chloroform to give the title compound 36 as a colorless solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give a residue which
  3. extractionextracted with chloroform (3×)
  4. washThe combined organic extracts are washed successively with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationConcentration
  7. customgives a solid which
  8. customis purified on silica gel eluting with 7/93 MeOH(NH3)/chloroform

Sources & evidence

ORD record
ord-28f9f6ad59b049ff9cae2cb3f055ea4a
Source dataset
uspto-grants-1997_07
Patent number
US05650535

Reaction notes

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