Sodium Bicarbonate → 4,5-Dimethyl-1H-benzimidazole

HRID 2105004Notes

Reaction equation

HRID 2105004 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([NH2:9])[C:3]=1[NH2:10].[C:11]([O-])(O)=O.[Na+]>C(O)=O.O>[CH3:1][C:2]1[C:3]2[N:10]=[CH:11][NH:9][C:4]=2[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 5210773,4-Dimethylbenzene-1,2-diamine

Product 1

HCID 135673414,5-Dimethyl-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

3,4-dimethylbenzene-1,2-diamine (300 mg) in 3 mL formic acid was irradiated in a microwave reactor at 150° C. for 5 min. The mixture was diluted with water, neutralized with sat. NaHCO3, then extracted with EtOAc (3×). The organic phase was washed with water and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated to afford 320 mg of Intermediate 178.1 as a tan solid. LCMS (2 min gradient) RT=0.90 min, 147.0 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a 1″ pad of silica gel
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c515623dbe374d78ac32e84b25ec6cf1
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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