Formic Acid → 4-Methylbenzimidazole

HRID 1970673Notes

Reaction equation

HRID 1970673 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

Conditions

Temperature
9 °C

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 9° 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. temperatureAfter cooling to 22 C
  2. customthe product was removed by filtration
  3. washwashed with water
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-b1065097638f422fa375bdc3e57933dc
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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