Propylamine → 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamide

HRID 1689611

Reaktionsgleichung

Reaktionsgleichung von HRID 1689611
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.[Na].[NH:17]1C2[C:22](=CC(S(O)(=O)=O)=CC=2)[C:20](=O)[C:18]1=O.O=P(Cl)(Cl)Cl.CCN(C(C)C)C(C)C.C(N)CC>C1COCC1.C(OCC)(=O)C>[CH2:18]([NH:17][S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13])[CH2:20][CH3:22]

Komponenten

9

Edukt 6

HCID 7852PropylamineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 817492,3-Dioxo-5-indolinesulfonic acidHCID 5360545SodiumHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Produkt 1

HCID 112771782,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonic acid propylamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonyl chloride (0.10 g, 0.41 mmol), prepared by the reaction of the sodium salt of 5-isatinsulfonic acid with POCl3, was dissolved in 5 mL THF. This solution was cooled in an ice bath and DIEA (0.14 mL, 2.0 eq) was added slowly, followed by n-propylamine (35 uL, 1.0 eq). Stirring was continued for 40 min and the solution was diluted with ethyl acetate and washed with brine. The organic layer was dried over Na2SO4 and the solvent was removed by evaporation. The residue was purified by SiO2 chromatography to give the title compound (65 mg, 60%).

Aufarbeitung

  1. temperatureThis solution was cooled in an ice bath
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent was removed by evaporation
  5. customThe residue was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-741ab8bdf9794660af893b58005f28d3
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153593B2

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