Hydrochloric Acid → 3,4-Diphenyl-1,2,5-thiadiazole-1,1-dioxide

HRID 1290614Notes

Reaction equation

HRID 1290614 reaction equation
[C:1]1([C:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:17]([NH2:21])([NH2:20])(=[O:19])=[O:18].Cl>C(O)C>[C:1]1([C:7]2[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:21][S:17](=[O:19])(=[O:18])[N:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8651BenzilHCID 82267Sulfamide

Product 1

HCID 110001093,4-Diphenyl-1,2,5-thiadiazole-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzil (10 g, 48 mmol) and sulfamide (4.6 g, 48 mmol) were combined in anhydrous, denatured ethanol (100 mL) and dry hydrogen chloride gas was bubbled into the reaction mixture until the temperature reached 55° C. The mixture was heated at reflux for 2 hrs, allowed to equilibrate and proceed overnight at room temperature. Concentration of the mixture gave a light yellow solid which was triturated first with water then with ether yielding 10.74 g (83%) of a white solid. The solids may be recrystallized if necessary from acetone to give white crystals.

Workup

  1. customwas bubbled into the reaction mixture until the temperature
  2. customreached 55° C
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 2 hrs
  5. customConcentration of the mixture gave a light yellow solid which
  6. customwas triturated first with water
  7. customThe solids may be recrystallized if necessary from acetone
  8. customto give white crystals

Sources & evidence

ORD record
ord-5893ecd3cdfa45d080941cf4c1042f68
Source dataset
uspto-grants-1998_05
Patent number
US05753599

Reaction notes

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