Formic Acid → 4-Methylbenzimidazole

HRID 327444

Reaction equation

HRID 327444 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-3592da26c31349c4ad925e57eefe2413
Source dataset
uspto-grants-1993_12
Patent number
US05273975

Linked notes

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