Pyridine → 2,4-Dinitrophenylbenzamide

HRID 986818

Reaction equation

HRID 986818 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1N)([O-:3])=[O:2].[C:14](Cl)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[N:23]1C=CC=CC=1>>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:14]([NH2:23])=[O:21])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 1049PyridineHCID 73212,4-DinitroanilineHCID 7412Benzoyl chloride

Product 1

HCID 201563782,4-Dinitrophenylbenzamide

Procedure

To a solution of 73.2 g. (0.4 m.) of 2,4-dinitroaniline in 400 ml. of pyridine with stirring and slight warming is added 56.2 g. (0.4 m.) of benzoyl chloride in about 10 min.; the temperature rises from 40° to 50°. Then the dark solution is heated at reflux for 21/2 hours. After standing overnight, the yellow solid is collected, washed with H2O until no pyridine odor is detectable. This 90 g. of crude product is recrystallized from about 2.1 of CH3CN to yield 44 g. (38%) of yellow product melting at 201°-205°.

Workup

  1. temperatureslight warming
  2. additionis added 56.2 g
  3. customrises from 40° to 50°
  4. temperatureThen the dark solution is heated
  5. temperatureat reflux for 21/2 hours
  6. customthe yellow solid is collected
  7. washwashed with H2O until no pyridine odor
  8. customof crude product is recrystallized from about 2.1 of CH3CN
  9. customto yield 44 g

Sources & evidence

ORD record
ord-7da71810bee64d97941cc6ab73feae9f
Source dataset
uspto-grants-1987_12
Patent number
US04716168

Linked notes

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