Benzenesulfonamide → 2,4-Dinitrobenzonitrile

HRID 1834037Notes

Reaction equation

HRID 1834037 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=O)([O-:3])=[O:2].C1(S([NH2:25])(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]#[N:25])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 118802,4-Dinitrobenzoic acidHCID 14798Sodium Hydroxide

Product 1

HCID 5540822,4-DinitrobenzonitrileYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 21.2 grams (0.1 mole) of 2,4-dinitrobenzoic acid and 32.0 grams (0.21 mole) of benzenesulfonamide is stirred and heated in an oil bath at 205°-210° for 1 hour and then at 225° for 1 hour and allowed to cool to room temperature under a nitrogen atmosphere. The residue is shaken with methylene chloride and dilute NaOH solution and the methylene chloride layer separated and washed with water. The solvent is removed by distillation. There is obtained 6.05 grams (31%) of material melting at 88°-92°. Recrystallization from ethanol raises the melting point to 100°-2°. The infrared spectrum shows a weak nitrile band at 2200 cm-1.

Workup

  1. temperatureheated in an oil bath at 205°-210° for 1 hour
  2. customthe methylene chloride layer separated
  3. washwashed with water
  4. customThe solvent is removed by distillation

Sources & evidence

ORD record
ord-0c5fbf31c9434809bc4063eaee3972d6
Source dataset
uspto-grants-1978_01
Patent number
US04067995

Reaction notes

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