Trimethylsilyldiazomethane → methyl 1H-1,3-benzodiazole-5-carboxylate

HRID 2300793Notes

Reaction equation

HRID 2300793 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([OH:12])=[O:11])=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO>[CH3:13][O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:1]=[CH:2][NH:3][C:4]=2[CH:9]=1)=[O:12]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 4594565-Benzimidazolecarboxylic acid

Product 1

HCID 2779733methyl 1H-1,3-benzodiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of benzimidazole-5-carboxylic acid (100 mg, 0.616 mmol, 1 eq) in MeOH (4 mL) was added a 2N solution of trimethylsilyldiazomethane in hexanes (3×0.3 mL, 1.8 mmol, 3 eq). Nitrogen evolution was evident. Eventually a yellow color persisted. The reaction was quenched by the addition of a small amount of acetic acid. The MeOH was removed under reduced pressure and the mixture was purified by preparative thin layer chromatography (eluted with 7% MeOH in CH2Cl2) giving 66 mg of the desired product.

Workup

  1. customThe reaction was quenched by the addition of a small amount of acetic acid
  2. customThe MeOH was removed under reduced pressure
  3. customthe mixture was purified by preparative thin layer chromatography (eluted with 7% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f766d6e5d79b4fc291a27aa69e3651f8
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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