Formic Acid → 4-Methylbenzimidazole

HRID 1648287Notes

Reaction equation

HRID 1648287 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[CH:10](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

3

Reactant 2

HCID 284Formic AcidHCID 175932,3-Diaminotoluene

Product 1

HCID 15193414-MethylbenzimidazoleYield 90%

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-1,2-benzenediamine (11.9 g) and formic acid (150 mL) was heated at 70° C. for 15 minutes. The solvent was removed under reduced pressure and the residual oil was stirred with water (100 mL) and sodium hydroxide solution (65 mL of 4.0 N) was added until the solution was just basic. The precipitate was filtered off, washed with water, and air dried to give 11.6 g (90%) of 4-methyl-1H-benzimidazole, mp 141°-145° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionwas added until the solution
  3. filtrationThe precipitate was filtered off
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-4b722371fbc240ae9945af69c86dbc7a
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

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