p-Toluenesulfonic acid → HCID 58243582, compound

HRID 389114Notes

Reaction equation

HRID 389114 reaction equation
[CH:1](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][C:24]=1[NH:34][CH3:35]>O1CCCC1>[CH2:30]([NH:29][C:27]([C:26]1[CH:32]=[CH:33][C:23]2[N:22]=[CH:35][N:34]([CH3:1])[C:24]=2[CH:25]=1)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 63360593HCID 63360593, compound

Product 1

HCID 58243582HCID 58243582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethyl orthoformate (4 ml) and p-toluenesulfonic acid (200 mg) were added to a solution of 4-amino-N-ethyl-3-(methylamino)benzamide (1.92 g) in tetrahydrofuran (40 ml), followed by heating to reflux for one hour. The solvent was evaporated under reduced pressure and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was washed with diisopropylether to obtain N-ethyl-1-methyl-1H-benzimidazole-6-carboxamide (1.16 g), as a colorless solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for one hour
  3. customThe solvent was evaporated under reduced pressure and water
  4. additionwas added
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. washThe resulting residue was washed with diisopropylether

Sources & evidence

ORD record
ord-5223faada68f4a27b0cb424afc357bd1
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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