2,3-Diaminotoluene → 4-Methylbenzimidazole

HRID 2104998Notes

Reaction equation

HRID 2104998 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10]([O-])(O)=O.[Na+]>C(O)=O.O>[CH3:1][C:2]1[C:3]2[N:9]=[CH:10][NH:8][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 175932,3-DiaminotolueneHCID 516892Sodium Bicarbonate

Product 1

HCID 15193414-Methylbenzimidazole

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 3-methylbenzene-1,2-diamine (170 mg) in formic acid (2 mL) was heated at 140° C. for 5 min in a microwave reactor. The mixture was diluted with water, neutralized with sat. NaHCO3, then extracted with EtOAc. The organic phase was washed with water and brine, dried (Na2SO4), filtered through a 1″ pad of silica gel and concentrated to afford 122 mg of Intermediate 171.1 as a tan solid.

Workup

  1. extractionextracted with EtOAc
  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-197fb0eeb1d34160b9f559c23e5a8a0c
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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