Hydrochloric Acid → 5-Amino-1,3,4-thiadiazole-2-sulfonamide

HRID 2190263Notes

Reaction equation

HRID 2190263 reaction equation
[S:1]([C:5]1[S:9][C:8]([NH:10]C(=O)C)=[N:7][N:6]=1)(=[O:4])(=[O:3])[NH2:2].Cl>CO>[NH2:10][C:8]1[S:9][C:5]([S:1]([NH2:2])(=[O:4])=[O:3])=[N:6][N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1986Acetazolamide

Product 1

HCID 847245-Amino-1,3,4-thiadiazole-2-sulfonamideYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide (1.0 g, 4.50 mmol) and MeOH (15 mL) was added HCl (2 N, 10 mL). The reaction mixture was heated at reflux for 18 hours and then concentrated under reduced pressure. The residue was purified by column chromatography (silica, 0-10% MeOH in CMA) to afford the sub-title compound (800 mg, 98%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (silica, 0-10% MeOH in CMA)

Sources & evidence

ORD record
ord-f0cba43ac8aa40e6994b3729b76c688f
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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