Cyclohexene → 6-Aminosaccharin

HRID 1038798

反応式

HRID 1038798 の反応式
[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

参加物

5

反応物 2

HCID 8079CyclohexeneHCID 1001876-Nitrosaccharin

生成物 1

HCID 647896-Aminosaccharin収率 80.7%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-91c88d7a164f44d9949e8315bb5eee91
出典データセット
uspto-grants-2013_10
特許番号
US08551981B2

関連ノート

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