2-(Azidomethyl)-1,3-benzoxazole → 1-(1,3-Benzoxazol-2-yl)methanamine

HRID 1736665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1736665
[N:1]([CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1)=[N+]=[N-]>[Pd].C(O)C>[NH2:1][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Komponenten

4

Edukt 1

HCID 229128932-(Azidomethyl)-1,3-benzoxazole

Produkt 1

HCID 14155281-(1,3-Benzoxazol-2-yl)methanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 8.28 g (47.5 mmol) of 2-(azidomethyl)benzoxazole (PREPARATION 5) and 0.526 g of 10% Palladium on charcoal in absolute ethanol (150 ml) is shaken under hydrogen at 36 psi for 40 min. The catalyst is then filtered off and the filtrate is concentrated. The crude product is chromatographed on silica gel (700 ml) eluting with methanol/dichloromethane (2/98), the appropriate fractions are pooled and concentrated to give the product. Crystallization from ethyl ether/hexane gives the title compound, mp 46.5°-47.5°; MS m/z) at 148; NMR (CDCl3) 1.70, 4.14, 7.33, 7.51, 7.70 δ.

Aufarbeitung

  1. filtrationThe catalyst is then filtered off
  2. concentrationthe filtrate is concentrated
  3. customThe crude product is chromatographed on silica gel (700 ml)
  4. washeluting with methanol/dichloromethane (2/98)
  5. concentrationconcentrated
  6. customto give the product
  7. customCrystallization from ethyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-dfef29d3360a44b58b32e2d49d47cbb2
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05541324

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