Hydrazine hydrate (1:1) → 4-((3-amino-1H-1,2,4-triazol-5-yl)amino)benzenesulfonamide

HRID 601064Notes

Reaction equation

HRID 601064 reaction equation
[C:1]([N:3]=[C:4](OC1C=CC=CC=1)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH2:15])(=O)=[O:13])=[CH:8][CH:7]=1)#[N:2].[OH2:23].[NH2:24][NH2:25]>C1COCC1>[NH2:2][C:1]1[NH:25][N:24]=[C:4]([NH:5][C:6]2[CH:7]=[CH:8][C:9]([S:12]([NH2:15])(=[O:13])=[O:23])=[CH:10][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178512286phenyl N'-cyano-N-(4-sulfamoylphenyl)carbamimidate

Product 1

HCID 113797954-((3-amino-1H-1,2,4-triazol-5-yl)amino)benzenesulfonamideYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-(3-cyano-2-phenyl-isoureido)-benzenesulfonamide (1.35 mmol) in THF (5 ml), was added a solution of hydrazine monohydrate (2 mmol; 1.5 equivalents). The solution was stirred at 70° C. for 16 hours. The reaction mixture was allowed to cool to room temperature. A white solid precipitated out. It was removed by filtration and was washed with ethanol to afford the title compound (300 mg; 87% yield). 1H NMR (400 MHz, DMSO-d6) 5.95-6.00 (2H, s), 7.00-7.05 (2H, s), 7.55-7.65 (4H, m), 9.15-9.20 (1H, s); MS (ES+) m/e=255

Workup

  1. temperatureto cool to room temperature
  2. customA white solid precipitated out
  3. customIt was removed by filtration
  4. washwas washed with ethanol

Sources & evidence

ORD record
ord-53e27f02dbba4af4a55931667e903f5f
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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