Hydrochloric Acid → HCID 178509071, compound

HRID 569698Notes

Reaction equation

HRID 569698 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[C:16]([NH:18]C(=O)C)[NH:15][N:14]=1)(=[O:12])=[O:11].Cl>C1COCC1>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[C:16]([NH2:18])[NH:15][N:14]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178474480HCID 178474480, compound

Product 1

HCID 178509071HCID 178509071, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 45.0 g (0.13 mol) of N-(2,6-dichlorophenyl)-5-acetamido-1,2,4-triazole-3-sulfonamide, 60 ml of 6N aqueous hydrochloric acid, and 500 ml of THF was heated at reflux for 4 hrs. The reaction mixture was cooled and the solvent was removed by rotary evaporation in vacuo. The crude solid was triturated with 5 ml of cold ethanol and then recrystallized from water. The desired product was collected by filtration and dried to yield 34.0 g (86 percent) of the desired product as a white solid, mp 262°-264° C. (decomposition). IR, 1H NMR, and 13C NMR were consistent with the assigned structure.

Workup

  1. temperatureat reflux for 4 hrs
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed by rotary evaporation in vacuo
  4. customThe crude solid was triturated with 5 ml of cold ethanol
  5. customrecrystallized from water
  6. filtrationThe desired product was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ee6d3bce11674c66bc190f517965b006
Source dataset
uspto-grants-1988_03
Patent number
US04734123

Reaction notes

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