Semicarbazide hydrochloride → HCID 20395322, compound

HRID 261238Notes

Reaction equation

HRID 261238 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:10](Cl)(=[O:12])=[O:11])[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8].Cl.[NH2:15][NH:16][C:17]([NH2:19])=[O:18].[OH-].[Na+]>CC(N(C)C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([S:10]([NH:15][NH:16][C:17]([NH2:19])=[O:18])(=[O:12])=[O:11])[CH:5]=[C:6]([CH3:9])[C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 14798Sodium HydroxideHCID 157100424-Hydroxy-3,5-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 20395322HCID 20395322, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

11 g (0.05 mol) of 3,5-dimethyl-4-hydroxybenzenesulphonic acid chloride and 6 g (0.05mol) of semicarbazide hydrochloride are first introduced into 50 ml of dimethylacetamide. 10 ml of 10 N sodium hydroxide solution are added dropwise to this white suspension over the course of 15 minutes at 40° C., whilst stirring. Since the reaction is exothermic, slight cooling must be applied. The mixture is then stirred for a further 4 hours at 40° C. After cooling to 0° C., the sodium chloride which has precipitated is filtered off and the filtrate is concentrated completely under reduced pressure. The residue is dissolved in a small amount of water and is cooled to 0°-5° C. Hereupon, 3.5-dimethyl-4-hydroxybenzenesulphonylsemicarbazide, of melting point 243° C. (with decomposition), crystallises out.

Workup

  1. temperatureslight cooling must
  2. stirringThe mixture is then stirred for a further 4 hours at 40° C
  3. customthe sodium chloride which has precipitated
  4. filtrationis filtered off
  5. concentrationthe filtrate is concentrated completely under reduced pressure
  6. dissolutionThe residue is dissolved in a small amount of water
  7. temperatureis cooled to 0°-5° C
  8. customHereupon, 3.5-dimethyl-4-hydroxybenzenesulphonylsemicarbazide, of melting point 243° C. (with decomposition), crystallises out

Sources & evidence

ORD record
ord-2f13a7581cb14b0fa94d16ee411735a8
Source dataset
uspto-grants-1979_08
Patent number
US04164611

Reaction notes

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