Hydrazine → N-(5-Amino-1,2,4-triazol-3-yl)-2-nitrobenzenesulfonamide

HRID 980512Notes

Reaction equation

HRID 980512 reaction equation
[C:1]([N:3]=[C:4](SC)[NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])#[N:2].[NH2:20][NH2:21]>C(#N)C>[NH2:2][C:1]1[NH:21][N:20]=[C:4]([NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[N:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 178503935methyl N-cyano-N'-(2-nitrophenyl)sulfonylcarbamimidothioate

Product 1

HCID 13772880N-(5-Amino-1,2,4-triazol-3-yl)-2-nitrobenzenesulfonamideYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 29.4 g (98.0 mmol) of N'-Cyano-N-(2-nitrophenylsulfonyl)-S-methylisothiourea in 100 ml of acetonitrile was treated with 6.2 ml (6.3 g, 0.20 mol) of anhydrous hydrazine. A mild exothermic reaction occurred as the reaction mixture became homogeneous. After stirring for 9 days the precipitated solid was collected by filtration and dried to afford 22.9 g of yellow solid. The crude product was recrystallized from HOAc to yield a total of 15.9 g (57 percent) of the desired product as a pale yellow solid, mp 255°-256° C. IR and 1H NMR spectra were consistent with the assigned structure.

Workup

  1. customA mild exothermic reaction
  2. filtrationwas collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-097c60612d5047d3bb1b7b2da28d485b
Source dataset
uspto-grants-1987_01
Patent number
US04638075

Reaction notes

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