Toluene → Methyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate

HRID 928446Notes

Reaction equation

HRID 928446 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:14].[C:15]1(C)C=CC=CC=1>CO>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([O:13][CH3:15])=[O:12])=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:14]

Participants

4

Reactant 2

HCID 1140TolueneHCID 8452601,2-Dimethyl-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 21998749Methyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1,2-Dimethyl-1H-benzo[d]imidazole-5-carboxylic acid (crude, 2.54 g, approx. 9.35 mmol) in MeOH (15.5 ml)/toluene (78 ml) Trimethylsilyldiazomethane (2 M solution in hexane, 7.0 ml, 14 mmol) was added at 0-10° C. The reaction mixture was stirred at it for 1 hour. The reaction mixture was evaporated under reduced pressure. The residue was taken up in DCM, Remaining insoluble solid was filtered off. The filtrate was evaporated again to dryness to afford crude Methyl 1,2-dimethyl-1H-benzo[d]imidazole-5-carboxylate

Workup

  1. additionwas added at 0-10° C
  2. customThe reaction mixture was evaporated under reduced pressure
  3. filtrationwas filtered off
  4. customThe filtrate was evaporated again to dryness

Sources & evidence

ORD record
ord-e526c639768d4100a852bb5e94a042d8
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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