Sodium Chloride → HCID 19901598, compound

HRID 2372688Notes

Reaction equation

HRID 2372688 reaction equation
C(#N)C.[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][CH:13]=[O:14])=[CH:7][CH:6]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[S:25](Cl)(=[O:27])=[O:26].[Cl-].[Na+]>CN(C)C(=O)C.N1C=CC=CC=1>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[S:25]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][NH:12][CH:13]=[O:14])=[CH:9][CH:10]=1)(=[O:27])=[O:26]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6342AcetonitrileHCID 206302-Chloro-5-nitrobenzenesulfonyl chlorideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 19901598HCID 19901598, compoundYield 72.6%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
-5 °C

Procedure

In a mixture of 90 ml of N,N-dimethylacetamide, 76 ml of acetonitrile, and 19 ml of pyridine were dissolved 35.4 g of 2-(4-aminophenyl)-1-formylhydrazine in a nitrogen gas atmosphere and after cooling the solution to -5° C., 59.9 g of 2-chloro-5-nitrobenzenesulfonyl chloride were gradually added to the solution while cooling the solution with stirring so that the liquid temperature was not over -5° C. After further stirring the mixture for 1.5 hours at a temperature below -5° C., the reaction mixture was poured into 1 liter of a saturated aqueous sodium chloride solution at room temperature. Crystals thus formed were collected by filtration and then washed with water to provide 63 g of the desired product.

Workup

  1. temperaturewhile cooling the solution
  2. customwas not over -5° C
  3. stirringAfter further stirring the mixture for 1.5 hours at a temperature below -5° C.
  4. customCrystals thus formed
  5. filtrationwere collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-75b43d0a828c4b7bb51dee4015156f85
Source dataset
uspto-grants-1992_03
Patent number
US05100761

Reaction notes

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