Hydrazine → N-(5-Amino-1,2,4-triazol-3-yl)-2,6-dichlorobenzenesulfonamide

HRID 1906302Notes

Reaction equation

HRID 1906302 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].CS[C:15](SC)=[N:16][C:17]#[N:18].C([O-])([O-])=O.[K+].[K+].[NH2:27][NH2:28]>C1COCC1>[NH2:18][C:17]1[NH:28][N:27]=[C:15]([NH:12][S:9]([C:3]2[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:11])[N:16]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 66289Dimethyl N-cyanodithioiminocarbonateHCID 27580592,6-Dichlorobenzenesulfonamide

Product 1

HCID 13772889N-(5-Amino-1,2,4-triazol-3-yl)-2,6-dichlorobenzenesulfonamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 90.1 g (0.398 mol) of 2,6-dichlorobenzenesulfonamide, 64.7 g (0.398 mol) of dimethyl N-cyanodithioiminocarbonate and 58.3 g (0.420 mol) of powdered anhydrous K2CO3 in 800 ml of THF was heated at reflux for 3 hours. After cooling to 30° C., 25.3 ml (25.6 g, 0.798 mol) of anhydrous hydrazine was added dropwise over 30 minutes. The resulting mixture was stirred for 3 days at ambient temperature and filtered. The solid collected was washed with THF, suspended in 400 ml of water and acidified with 180 ml of acetic acid. The resulting mixture was filtered, and the solid collected was washed with water and dried to yield 112 g (91 percent) of the desired product as a white solid, mp 300° C. (decomp.) IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. filtrationfiltered
  4. customThe solid collected
  5. washwas washed with THF
  6. filtrationThe resulting mixture was filtered
  7. customthe solid collected
  8. washwas washed with water
  9. customdried

Sources & evidence

ORD record
ord-f1c62a3f5bf7459ea6ce511d411fb5f3
Source dataset
uspto-grants-1987_03
Patent number
US04650892

Reaction notes

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