Pyridine → 3-[[(4-Nitrophenyl)sulfonyl]amino]benzamide

HRID 27365

Reaction equation

HRID 27365 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1)([O-:13])=[O:12].N1C=CC=CC=1>C(O)(=O)C>[N+:11]([C:14]1[CH:15]=[CH:16][C:17]([S:20]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:7])=[O:6])(=[O:22])=[O:21])=[CH:18][CH:19]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 16453-AminobenzamideHCID 74044-Nitrobenzenesulfonyl chloride

Product 1

HCID 233427083-[[(4-Nitrophenyl)sulfonyl]amino]benzamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution containing 44 g (0.32 m) of 3-aminobenzamide, 71.6 g (0.32 m) of p-nitrobenzenesulfonyl chloride and 700 ml of pyridine was stirred and heated on a steam bath for 2.5 hours, then poured into ice water. Acetic acid was added to a pH 5.0-6.0 and the resulting solid collected by filtration, washed with water and air-dried to give 105 g, m.p. 240°-244°.

Workup

  1. temperatureheated on a steam bath for 2.5 hours
  2. filtrationthe resulting solid collected by filtration
  3. washwashed with water
  4. customair-dried
  5. customto give 105 g, m.p. 240°-244°

Sources & evidence

ORD record
ord-bbd816c868a14927a1a9ed82fa64f9fe
Source dataset
uspto-grants-1980_09
Patent number
US04221730

Linked notes

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