Hydrazine hydrate (1:1) → N-(5-Amino-1,2,4-triazol-3-yl)-2,5-dichlorobenzenesulfonamide

HRID 980515Notes

Reaction equation

HRID 980515 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][S:6]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[Cl:16])(=[O:8])=[O:7])#[N:2].O.[NH2:20][NH2:21]>C(O)C>[NH2:2][C:1]1[NH:21][N:20]=[C:4]([NH:5][S:6]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[Cl:16])(=[O:8])=[O:7])[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178503936HCID 178503936, compound

Product 1

HCID 13772881N-(5-Amino-1,2,4-triazol-3-yl)-2,5-dichlorobenzenesulfonamideYield 63.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8.51 g (26.2 mmol) of N'-cyano-N-(2,5-dichlorophenylsulfonyl)-S-methylisothiourea and 10 ml (10 g, 0.20 mol) of hydrazine monohydrate in 85 ml of ethanol was heated at reflux for 30 minutes. After cooling to room temperature, the solid which separated was collected and suspended in 170 ml of H2O and the suspension was acidified with concentrated aqueous HCl. After stirring the suspension for 4 hours the solid was collected and dried in vacuo to yield 5.10 g (57 percent) of the desired product as a hydrochloride salt, mp 306°-308° C. IR and 1H NMR spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. customthe solid which separated
  4. customwas collected
  5. customwas collected
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9cf063335031430398e954037996be8f
Source dataset
uspto-grants-1987_01
Patent number
US04638075

Reaction notes

Loading…