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

HRID 383744

반응식

HRID 383744 반응식
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

참가 물질

4

반응물 2

HCID 1986AcetazolamideHCID 14797Potassium Hydroxide

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
100 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-eac7847c991a4b0b9a677c2e6845d442
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367667B2

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