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2-Morpholinoethylamine → 5-(2-Morpholinoethylaminosulphonyl)oxindole

HRID 1386330
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1386330
Cl[S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:14])[CH2:8]2)(=[O:4])=[O:3].[NH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)C>[O:21]1[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][NH:15][S:2]([C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][C:9](=[O:14])[CH2:8]3)(=[O:4])=[O:3])[CH2:19][CH2:20]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4082852-MorpholinoethylamineHCID 49625062-oxo-2,3-dihydro-1H-indole-5-sulfonyl chloride

Produkt 1

HCID 217173035-(2-Morpholinoethylaminosulphonyl)oxindoleAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A solution of 5-chlorosulphonyloxindole (1 g, 4.3 mmol), (prepared as described for the starting material in Example 60), and 4-(2-aminoethyl)morpholine (620 μl, 4.7 mmol) in ethanol (20 ml) was heated at 65° C. for 1 hour. The solvent was removed by evaporation, the residue was partitioned between methylene chloride and water and the aqueous layer was adjusted to pH7-8 with 5% aqueous sodium hydrogen carbonate solution. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 5-(2-morpholinoethylaminosulphonyl)oxindole (750 mg, 54%).

Aufarbeitung

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/methanol (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-e1fa01c8a58441a5acca466ca14cb5fd
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06265411B1

Notizen zur Reaktion

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