Water → isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester

HRID 2120260

Reaktionsgleichung

Reaktionsgleichung von HRID 2120260
[OH:1][CH2:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][C:7](=[O:13])[NH:8]2.[CH:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15].O>O1CCCC1.CN(C)C=O>[O:13]=[C:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[CH:12][C:4]=2[CH2:3][CH2:2][O:1][C:18](=[O:19])[NH:17][CH:14]([CH3:16])[CH3:15])[NH:8]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 61277Isopropyl isocyanateHCID 109430044-(2-Hydroxyethyl)indolin-2-one

Produkt 1

HCID 9903356isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl esterAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (3 g, 16.93 mmol) and isopropyl isocyanate (2.49 mL, 25.40 mmol) in tetrahydrofuran (16 mL) and dimethylformamide (6 mL) was heated at 80° C. for 64 hours. The reaction mixture was poured into water and extracted with ethyl acetate (400 mL), washed with brine, dried (sodium sulfate), and concentrated. The residue was recrystallized form methanol, ethyl acetate and hexanes to give 1.136 g (26%) of isopropyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester as crystalline solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (400 mL)
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe residue was recrystallized form methanol, ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9a2237619a824b71920dc83e5ba446ff
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06689806B1

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