Formic Acid → 4-Methylbenzimidazole

HRID 1983923Notes

Reaction equation

HRID 1983923 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].Cl.[OH-].[NH4+].[CH:13](O)=O>>[CH3:9][C:3]1[C:2]2[N:1]=[CH:13][NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 175932,3-Diaminotoluene

Product 1

HCID 15193414-Methylbenzimidazole

Procedure

To a flask were added 2.0 g 2,3-diaminotoluene, 1.0 g 90% formic acid and 30 ml 5M hydrochloric acid and the mixture was heated to 90 C under nitrogen for 4 hours. After cooling to 22 C, the mixture was basified with aqueous ammonium hydroxide and the product was removed by filtration and washed with water. The product was purified by column chromatography using pure ethyl acetate resulting in 1.0 g brown solid.

Workup

  1. temperaturethe mixture was heated to 90 C under nitrogen for 4 hours
  2. temperatureAfter cooling to 22 C
  3. customthe product was removed by filtration
  4. washwashed with water
  5. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-e16537518805484fb8091f50e584f5b3
Source dataset
uspto-grants-2009_06
Patent number
US07542196B2

Reaction notes

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