Acetazolamide → 5-Amino-1,3,4-thiadiazole-2-sulfonamide

HRID 912575

Reaction equation

HRID 912575 reaction equation
CC([NH:4][C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:7][N:6]=1)=O.[OH-].[K+]>Cl>[NH2:4][C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[N:7][N:6]=1

Participants

4

Reactant 2

HCID 1986AcetazolamideHCID 14797Potassium Hydroxide

Product 1

HCID 847245-Amino-1,3,4-thiadiazole-2-sulfonamideYield 72.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

Acetazolamide (2.03 g, 9.13 mmol) was combined with 1N HCl (20 mL) and then heated at 100° C. The initial suspension became a clear solution within 3h. After cooling to 0° C. the reaction mixture was carefully neutralized by the addition of solid KOH. Upon standing precipitates had formed and were collected by filtration. The solids were dried under high vacuum to afford 5-amino-[1,3,4]thiadiazole-2-sulfonic acid amide (1.2 g, 70%) as a colorless solid; 1H NMR (DMSO-d6): δ 8.06 (s, 2H), 7.82 (s, 2H). Acetazolamide (2.03 g, 9.13 mmol) was combined with 1 N HCl (20 mL) and then heated at 100° C. The initial suspension became a clear solution within 3h. After cooling to 0° C. A.

Workup

  1. customwithin 3h
  2. temperatureAfter cooling to 0° C. the reaction mixture
  3. customUpon standing precipitates
  4. customhad formed
  5. filtrationwere collected by filtration
  6. customThe solids were dried under high vacuum

Sources & evidence

ORD record
ord-5d84373e38b24444bdf252184c130f7c
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Linked notes

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