Formic Acid → 4,7-Dimethyl-1H-benzo[d]imidazole

HRID 2295045Notes

Reaction equation

HRID 2295045 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][C:3]=1[CH3:10].[CH:11](O)=O.Cl.[OH-].[NH4+]>O>[CH3:9][C:6]1[C:7]2[NH:8][CH:11]=[N:1][C:2]=2[C:3]([CH3:10])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 37769873,6-Dimethylbenzene-1,2-diamine

Product 1

HCID 130708274,7-Dimethyl-1H-benzo[d]imidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2,3-diamino-p-xylene (5.1 g), formic acid (88%, 200 mL) and 12N HCl (20 mL) is heated to reflux for 3 hours. The resulting mixture is cooled to room temperature and rotary evaporated. The residue is diluted with water (100 mL), then basified with ammonium hydroxide (28-30%). The suspension is extracted with ethyl acetate (3×100 mL). The combined extracts are dried over MgSO4 and rotary evaporated to afford 4,7-dimethylbenzimidazole as a yellow solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 hours
  3. extractionThe suspension is extracted with ethyl acetate (3×100 mL)
  4. dry with materialThe combined extracts are dried over MgSO4
  5. customrotary evaporated

Sources & evidence

ORD record
ord-cb473b38fcd141cf8de1a06a04017d02
Source dataset
uspto-grants-1997_11
Patent number
US05691370

Reaction notes

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