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

Temperatur

100 °C

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 3 h. 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 1N HCl (20 mL) and then heated at 100° C. The initial suspension became a clear solution within 3 h. After cooling to 0° C. A. The title compound was prepared from 5-amino-[1,3,4]thiadiazole-2-sulfonic acid amide in a manner similar to that described in Example 1D; 1H NMR (DMSO-d6): δ 8.09 (s, 2H), 7.82 (d, J=8 Hz, 1H), 7.73 (t, J=8 Hz, 1H), 7.63 (t, J=8 Hz, 1H), 7.32 (d, J=8 Hz, 1H), 6.74 (s, 1H), 1.98 (s, 3H), 1.67 (s, 3H); MS (ESI) m/z 446 [M+H]+.

1. customwithin 3 h
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

ORD-Eintrag

ord-eac7847c991a4b0b9a677c2e6845d442

Quelldatensatz

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08367667B2