Methanol → 5,6-Dimethyl 1H-benzimidazole-5,6-dicarboxylate

HRID 2300800Notes

Reaction equation

HRID 2300800 reaction equation
[N:1]1[C:5]2[CH:6]=C(C(O)=O)[C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.C[CH2:17][O:18][CH2:19][CH3:20].C[Si](C=[N+]=[N-])(C)C.[OH2:28].[CH3:29]O>CCOC(C)=O>[CH3:17][O:18][C:19]([C:20]1[C:8]([C:10]([O:12][CH3:29])=[O:11])=[CH:9][C:4]2[N:3]=[CH:2][NH:1][C:5]=2[CH:6]=1)=[O:28]

Participants

7

Reactant 5

HCID 887MethanolHCID 962WaterHCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 7023591benzimidazole-5,6-dicarboxylic acid

Product 1

HCID 106334195,6-Dimethyl 1H-benzimidazole-5,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 200 mg of 5,6-benzimidazoledicarboxylic acid dissolved in 2.0 mL of MeOH and 2.0 mL of diethyll ether was added 4 mL of trimethylsilyldiazomethane [2.0 M in hexanes]. The resulting solution was stirred for 1 hour before dilution with 20 mL of H2O and extraction with 2×10 mL of EtOAc. the organic phases were dried over MgSO4 and concentrated under reduced pressure. Column chromatography (SiO2, 5% MeOH in CH2Cl2) yielded 210 mg of the title compound as a yellow oil. Mass Spectrum (ESI) 231 (M+1).

Workup

  1. dry with materialthe organic phases were dried over MgSO4
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee32cbd92a954e7a946ecd479b859eec
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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