Cyclohexene → 6-Aminosaccharin

HRID 1038798

반응식

HRID 1038798 반응식
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=1)([O-])=O.C1CCCCC=1>CCO.[Pd]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=1

참가 물질

5

반응물 2

HCID 8079CyclohexeneHCID 1001876-Nitrosaccharin

생성물 1

HCID 647896-Aminosaccharin수율 80.7%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of 6-nitro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one (11.4 g, 50.0 mmol) and cyclohexene (25.4 mL, 250 mmol) in EtOH (100 mL) was added 5% Pd—C (35 g) at about 0° C. The mixture was refluxed overnight with stirring and then cooled to rt, filtered through Celite® several times until the filtrate became clear. The filtrate was concentrated under reduced pressure. The material was dissolved in saturated aqueous NaHCO3 (200 mL), filtered and to the filtrate was added concentrated hydrochloric acid (pH=7). The precipitate was collected by filtration and washed with water (2×50 mL) to provide 6-amino-1,2-benzisothiazol-3(2H)-one-1,1-dioxide (8.0 g, 68%): 1H NMR (DMSO-d6) δ: 7.61 (s, 1H), 7.59 (s, 1H), 6.95 (d, J=2.0 Hz, 2H), 6.91 (d, J=2.4 Hz, 1H), 6.89 (d, J=2.0 Hz, 1H).

후처리

  1. temperatureThe mixture was refluxed overnight
  2. filtrationfiltered through Celite® several times until the filtrate
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. dissolutionThe material was dissolved in saturated aqueous NaHCO3 (200 mL)
  5. filtrationfiltered and to the filtrate
  6. additionwas added concentrated hydrochloric acid (pH=7)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water (2×50 mL)

출처 및 근거

ORD 기록
ord-91c88d7a164f44d9949e8315bb5eee91
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08551981B2

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