Hydrazine hydrate (1:1) → 4-Hydroxy-3,5-dimethylbenzene-1-sulfonohydrazide

HRID 261239Notes

Reaction equation

HRID 261239 reaction equation
O.[NH2:2][NH2:3].CC(N(C)C)=O.[CH3:10][C:11]1[CH:12]=[C:13]([S:19](Cl)(=[O:21])=[O:20])[CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17]>O1CCOCC1>[CH3:10][C:11]1[CH:12]=[C:13]([S:19]([NH:2][NH2:3])(=[O:21])=[O:20])[CH:14]=[C:15]([CH3:18])[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 31374DimethylacetamideHCID 157100424-Hydroxy-3,5-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 203953194-Hydroxy-3,5-dimethylbenzene-1-sulfonohydrazide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

15.0 g (0.3 mol) of hydrazine hydrate are first introduced into 60 ml of dimethylacetamide. 22 g (0.1 mol) of 3,5-dimethyl-4-hydroxybenzenesulfonic acid chloride dissolved in 60 ml of dioxane are added dropwise to this solution over the course of 15 minutes. This causes the temperature to rise to 90° C., at which level it is maintained by slight cooling. The mixture is allowed to react for a further 90 minutes and is then completely concentrated under reduced pressure. The residue is recrystallised first from a little water and then from isopropanol. This gives 3,5-dimethyl-4-hydroxybenzenesulphonic acid hydrazide, which melts at 186° C. (with decomposition).

Workup

  1. additionare added dropwise to this solution over the course of 15 minutes
  2. customto rise to 90° C., at which level it
  3. temperatureis maintained by slight cooling
  4. customto react for a further 90 minutes
  5. concentrationis then completely concentrated under reduced pressure
  6. customThe residue is recrystallised first from a little water

Sources & evidence

ORD record
ord-c2c7b5f2d4f84b67b8149642a745b3e1
Source dataset
uspto-grants-1979_08
Patent number
US04164611

Reaction notes

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