Cyclopentylamine → 4-Bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide

HRID 1510427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510427
[Br:1][C:2]1[C:3]([C:14]([O:16]CC)=O)=[N:4][O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[CH:19]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20]1>C(O)C>[Br:1][C:2]1[C:3]([C:14]([NH:24][CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:16])=[N:4][O:5][C:6]=1[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 2906CyclopentylamineHCID 67121165Ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate

Produkt 1

HCID 533260944-Bromo-5-(4-chlorophenyl)-N-cyclopentylisoxazole-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 4-bromo-5-(4-chlorophenyl)isoxazole-3-carboxylate (213 mg, 0.70 mmol) and cyclopentylamine (0.70 mL, 7.0 mmol) in absolute ethanol (8 mL) was heated to reflux overnight. The volatiles were removed in vacuo and the compound was purified by silica gel chromatography eluting with 2% methanol with dichloromethane to afford the title compound: (0.21 g, 0.57 mmol). MS (ESI) m/z (M+H+): 370.9/368.8.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customThe volatiles were removed in vacuo
  4. customthe compound was purified by silica gel chromatography
  5. washeluting with 2% methanol with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1dc88497cf854c18aed5c14a1643c623
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211927B2

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