Water → N-[4-(2-Formylhydrazinyl)phenyl]-3-nitrobenzene-1-sulfonamide

HRID 848198Notes

Reaction equation

HRID 848198 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][CH:10]=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1)([O-:21])=[O:20].O>C(#N)C>[CH:10]([NH:9][NH:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:28]([C:24]2[CH:25]=[CH:26][CH:27]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)(=[O:29])=[O:30])=[CH:7][CH:6]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 15044312N-[4-(2-Formylhydrazinyl)phenyl]-3-nitrobenzene-1-sulfonamideYield 44.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

15.1 g of 2-(4-aminophenyl)-1-formylhydrazine and 14 ml of triethylamine were dispersed in 50 ml of acetonitrile. To the dispersion, a solution containing 50 ml of acetonitrile and 22.1 g of 3-nitrobenzenesulfonyl chloride was added dropwise while stirring at room temperature. After heating at 60° C. for 2 hours, the reaction mixture was cooled and then poured into water. The resulting crystals were collected by filtration. 15 g of the object compound was obtained.

Workup

  1. additionwas added dropwise
  2. temperatureAfter heating at 60° C. for 2 hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-0a4079ebe3cb4bf28c58b3a6ce2e372c
Source dataset
uspto-grants-1981_10
Patent number
US04294919

Reaction notes

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