Acetic Acid → 2-(m-Ethylphenyl)benzimidazole

HRID 1449028

Reaction equation

HRID 1449028 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:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[C:14]#N)[CH3:10].C[O-].[Na+].C(O)(=O)C>CO.O>[CH2:9]([C:11]1[CH:12]=[C:13]([C:14]2[NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[N:8]=2)[CH:16]=[CH:17][CH:18]=1)[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7243O-PhenylenediamineHCID 96692Benzonitrile, 3-ethyl-HCID 10942334Sodium Methoxide

Product 1

HCID 203477992-(m-Ethylphenyl)benzimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2.2 g. of o-phenylenediamine and 3.1 g. of m-ethylbenzonitrile were dissolved in 30 ml. of methanol. To the solution was added 1.1 g. of sodium methoxide in methanol. The mixture was stirred at 60° C. for 2 hours, acidified with acetic acid, stirred again at 100° C. for additional 3 hours and poured in 100 ml. of water. The resulting crystals were filtered off, dried and recrystallized from ethyl acetate. 2.7 g. of the product (60% of theory) was obtained. The product was identical to that obtained in Example 23.

Workup

  1. additionTo the solution was added 1.1 g
  2. stirringstirred again at 100° C. for additional 3 hours
  3. additionpoured in 100 ml
  4. filtrationThe resulting crystals were filtered off
  5. customdried
  6. customrecrystallized from ethyl acetate
  7. customof the product (60% of theory) was obtained
  8. customthat obtained in Example 23

Sources & evidence

ORD record
ord-9a49a61c1298479496cbdb29f4b4d733
Source dataset
uspto-grants-1980_02
Patent number
US04188486

Linked notes

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