Methanesulfonyl chloride → 5-Methanesulfonamidobenzothiophene

HRID 1086857

Reaktionsgleichung

Reaktionsgleichung von HRID 1086857
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)([O-])=O.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(O)C.[Pd]>[CH3:13][S:14]([NH:1][C:4]1[CH:5]=[CH:6][C:7]2[S:11][CH:10]=[CH:9][C:8]=2[CH:12]=1)(=[O:16])=[O:15]

Komponenten

5

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 124140845-Nitro-1-benzothiophene

Produkt 1

HCID 149860045-MethanesulfonamidobenzothiopheneAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5.00 g (0.028 mol) of 5-nitrobenzothiophene (Bordwell, J. Am. Chem. Soc., 77, 5939 (1955)) in 175 mL of ethanol was hydrogenated at 50 psi over 0.5 g of 10% Pd/c for 1.5 hours. The catalyst was removed by filtration, and the solvent was removed under reduced pressure. The residue, 4.39 g, was dissolved in a mixture of 8.4 g of pyridine and 50 mL of methylene chloride. The solution, treated with 3.45 g (0.03 mol) of methanesulfonyl chloride, was stirred overnight at room temperature. The solution was washed with water, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give 1.74 g of crystalline 5-methanesulfonamidobenzothiophene.

Aufarbeitung

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue, 4.39 g, was dissolved in a mixture of 8.4 g of pyridine and 50 mL of methylene chloride
  4. washThe solution was washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cefa3ae0700e4382a938f2c15691f8bd
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05032598

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