Chlorosulfonyl isocyanate → 6-Nitro-1H-indole-3-carbonitrile

HRID 468388

Reaktionsgleichung

Reaktionsgleichung von HRID 468388
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClS([N:17]=[C:18]=O)(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C.CC#N>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:18]#[N:17])=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 70918Chlorosulfonyl isocyanateHCID 785026-Nitro-1H-indoleHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2831796-Nitro-1H-indole-3-carbonitrileAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 6-nitroindole (4.9 g 30 mmol) in DMF (24 mL) and CH3CN (240 mL) was added dropwise a solution of ClSO2NCO (5.0 mL) in CH3CN (39 mL) at 0° C. After addition, the reaction was allowed to warm to room temperature and was stirred for 2 h. The mixture was then poured into ice-water and basified with sat, NaHCO3 solution to pH 7-8. The mixture was extracted with ethyl acetate. The organics were washed with brine, dried over Na2SO4 and concentrated to give 6-nitro-1H-indole-3-carbonitrile (4.6 g, 82%).

Aufarbeitung

  1. additionAfter addition
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9554f48720404e48ac290cebd739065e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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