Benzoyl chloride → HCID 178423990, compound

HRID 596572Notes

Reaction equation

HRID 596572 reaction equation
[N:1]#[C:2]N.[C:4](Cl)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:13][C:14]1[C:15]([NH2:21])=[C:16]([NH2:20])[CH:17]=[CH:18][CH:19]=1>N1C=CC=CC=1>[CH3:13][C:14]1[C:15]2[NH:21][C:2]([NH:1][C:4](=[O:11])[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=3)=[N:20][C:16]=2[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 9864CyanamideHCID 175932,3-Diaminotoluene

Product 1

HCID 178423990HCID 178423990, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Cyanamide (3.44 g.) is dissolved in 69 ml. of pyridine and the mixture is held at 0°-4° C. While stirring, benzoyl chloride (11.5 g.) is added in portions. The reaction mixture is maintained at 0°-4° C. for 15 minutes. 3-Methyl-o-phenylenediamine (10 g.) is then added to the reaction mixture, and the resulting product is kept at room temperature for a few hours and then heated on a steam-bath for about 2.5 hours. After cooling to room temperature, the mixture is evaporated under reduced pressure, poured into 200 ml. water, and rubbed until solid. The product is removed by suction-filtration, dissolved in 5% aqueous sodium hydroxide solution, and clarified by gravity filtration. The benzimidazole derivative is precipitated by the addition of the alkaline solution to a slight excess of dilute acetic acid.

Workup

  1. customis held at 0°-4° C
  2. temperatureThe reaction mixture is maintained at 0°-4° C. for 15 minutes
  3. waitthe resulting product is kept at room temperature for a few hours
  4. temperatureheated on a steam-bath for about 2.5 hours
  5. customthe mixture is evaporated under reduced pressure
  6. additionpoured into 200 ml
  7. customThe product is removed by suction-filtration
  8. dissolutiondissolved in 5% aqueous sodium hydroxide solution
  9. filtrationclarified by gravity filtration
  10. customThe benzimidazole derivative is precipitated by the addition of the alkaline solution to a slight excess of dilute acetic acid

Sources & evidence

ORD record
ord-cd6d3d48208d46309e6ad67ea1dcc996
Source dataset
uspto-grants-1977_03
Patent number
US04011236

Reaction notes

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