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

HRID 1709956Notes

Reaction equation

HRID 1709956 reaction equation
CN(C)C(=O)C.C(#N)C.C(N(CC)CC)C.[N+:17]([C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18].[NH2:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][NH:38][CH:39]=[O:40])=[CH:33][CH:32]=1>>[N+:17]([C:20]1[CH:21]=[C:22]([S:26]([NH:30][C:31]2[CH:32]=[CH:33][C:34]([NH:37][NH:38][CH:39]=[O:40])=[CH:35][CH:36]=2)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

6

Reactant 5

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 31374DimethylacetamideHCID 113189Hydrazinecarboxaldehyde, 2-(4-aminophenyl)-

Product 1

HCID 15044312N-[4-(2-Formylhydrazinyl)phenyl]-3-nitrobenzene-1-sulfonamide

Conditions

Temperature
-5 °C

Procedure

1 1 of N,N-dimethylacetoamide, 880 g of acetonitrile, and 285 g of triethylamine were added to and dissolved in 426 g of 2-(4-aminophenyl)-1-formylhydrazine under an atmosphere of nitrogen. The solution was cooled to -5° C., and 625 g of meta-nitrobenzenesulfonyl chloride was gradually added to the solution. During the addition, the mixture was agitated under cooling so that the temperature did not exceed -5° C. The resultant mixture was cooled at a temperature below -5° C. for 1.5 hours, then the temperature thereof was raised to a room temperature. Extraction was performed with 12 l of ethyl acetate and 12 l of saturated salt water. The organic layer was separated and then concentrated to 6 l. 3 l of n-hexane was added to the concentrate, and the obtained mixture was agitated at a room temperature for 30 minutes. The produced crystals were filtered off and washed with 500 g of ethyl acetate.

Workup

  1. additionDuring the addition
  2. temperatureunder cooling so that the temperature
  3. customdid not exceed -5° C
  4. temperaturethe temperature thereof was raised to a room temperature
  5. extractionExtraction
  6. customThe organic layer was separated
  7. concentrationconcentrated to 6 l
  8. addition3 l of n-hexane was added to the concentrate
  9. stirringthe obtained mixture was agitated at a room temperature for 30 minutes
  10. filtrationThe produced crystals were filtered off
  11. washwashed with 500 g of ethyl acetate

Sources & evidence

ORD record
ord-0bf31fcb2abe4d74926242db5cb6b0fa
Source dataset
uspto-grants-1990_08
Patent number
US04952483

Reaction notes

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