Cyclohexene → 6-Aminosaccharin

HRID 1038798

Reaction equation

HRID 1038798 reaction equation
[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

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 1001876-Nitrosaccharin

Product 1

HCID 647896-AminosaccharinYield 80.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-91c88d7a164f44d9949e8315bb5eee91
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Linked notes

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