O-Phenylenediamine → 2-(4-ethylphenyl)-1H-benzimidazole

HRID 1701307Notes

Reaction equation

HRID 1701307 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1)[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:9]([C:11]1[CH:19]=[CH:18][C:14]([C:15]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)=[CH:13][CH:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 10340Sodium CarbonateHCID 120864-Ethylbenzoic Acid

Product 1

HCID 7355142-(4-ethylphenyl)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.5 g. of o-phenylenediamine, 7.6 g. of p-ethylbenzoic acid and 40 g. of polyphosphoric acid were heated at 160°-180° C. under nitrogen gas current with stirring for 4 hours. The reaction mixture was diluted with 400 ml. of water and then neutralized with sodium carbonate. The resulting crystals were filtered off, dried and recrystallized from ethyl acetate. 8.2 g. (73% of theory) of the product was obtained. M.P. 258°-258.4° C.

Workup

  1. additionThe reaction mixture was diluted with 400 ml
  2. filtrationThe resulting crystals were filtered off
  3. customdried
  4. customrecrystallized from ethyl acetate
  5. custom(73% of theory) of the product was obtained

Sources & evidence

ORD record
ord-8e97f9fc2e5f41be860ef9995f3f38ef
Source dataset
uspto-grants-1980_03
Patent number
US04192880

Reaction notes

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