1-Hydroxy-6-methylsulfonylindole → 6-methanesulfonyl-1H-indole

HRID 1371958

Reaktionsgleichung

Reaktionsgleichung von HRID 1371958
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2O)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>P(OCC)(OCC)OCC.C(OCC)C>[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

4

Edukt 1

HCID 7035381-Hydroxy-6-methylsulfonylindole

Produkt 1

HCID 27610676-methanesulfonyl-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 31215Triethyl phosphiteLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Dissolve 6-Methanesulfonyl-indol-1-ol (5.0 g, 23.7 mmol) in triethyl phosphite (35 ml) and heat at 160° C. for 5 hours. Cool the solution to ambient temperature and dilute with diethyl ether. Wash the ether solution with brine and water followed by drying (sodium sulfate) and reducing to residue. Crystallize the residue from warm ethyl acetate to give the title compound as colorless cubes: mp 149–152° C. MS (ACPI): m/e 196.0 (M+1). Analysis for C9H9NO2S: Calcd: C, 55.37; H, 4.65; N, 7.17; found: C, 55.14; H, 4.71; N, 7.20.

Aufarbeitung

  1. temperatureCool the solution to ambient temperature
  2. washWash the ether solution with brine and water
  3. dry with materialby drying (sodium sulfate)
  4. customCrystallize the residue
  5. temperaturefrom warm ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d9a31402847d495ba9abaf5773d1d913
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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