4-Methoxybenzylamine → 2-methyl-1H-benzimidazole-5-carboxylic acid

HRID 2099855Notes

Reaction equation

HRID 2099855 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.OC1C2N=NNC=2C=CC=1.Cl.C(N=C=NCCCN(C)C)C.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][NH2:45])=[CH:40][CH:39]=1>CN(C)C=O>[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH2:44][NH-:45])=[CH:40][CH:39]=1.[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 754524-MethoxybenzylamineHCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 2

HCID 11326092-methyl-1H-benzimidazole-5-carboxylic acidYield 127%HCID 57878451HCID 57878451, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a dimethylformamide (20 ml) solution of 2-methylbenzimidazol-5-carboxylic acid (1.00 g) were added hydroxybenzotriazole (844 mg), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (1.21 g) and 4-methoxyphenylmethylamine (1.33 g) at room temperature, and the reaction solution was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure and the obtained residue was diluted with chloroform (20 ml). The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The residue obtained by solvent evaporation under reduced pressure was subjected to silica gel column chromatography and eluted with chloroform-methanol (30:1 (v/v)) to obtain (4-methoxyphenylmethyl)amide of 2-methyl-1H-benzimidazol-5-carboxylic acid (1.27 g, 99%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe obtained residue was diluted with chloroform (20 ml)
  3. washThe organic layer was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained by solvent evaporation under reduced pressure
  6. washeluted with chloroform-methanol (30:1 (v/v))

Sources & evidence

ORD record
ord-071c4b37e4c94153a634d1906011744a
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

Loading…