Reaktion #1615524

ord-c69e3b2b68314075b07885a671a09263

Reaktionsgleichung

N#C/C(=N\OCc1csc(N)n1)c1ccccc1
(2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile
Cl.NO
hydroxylamine hydrochloride
O=C([O-])[O-].[K+].[K+]
potassium carbonate
NC(=N\O)/C(=N\OCc1csc(N)n1)c1ccccc1
(1Z,2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide
Ausbeute 115.5%

Lösungsmittel

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solvent was evaporated to ¾th
  2. 2
    ExtraktionThe residue was extracted with EtOAc (3×50 ml)
  3. 3
    Waschenwashed with aq. sat. NaCl
  4. 4
    Trocknendried over MgSO4
  5. 5
    Einengenconcentrated

Vorschrift

To a suspension of (2Z)-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}(phenyl)acetonitrile (4.5 g, 17.42 mmol, 1 eq.) in iPrOH/H2O (10/1, 110 ml) were added hydroxylamine hydrochloride (3.63 g, 52.26 mmol, 3 eq.) and potassium carbonate (7.22 g, 52.2 mmol, 3 eq.). The reaction was heated to 80° C. for 6 h and the solvent was evaporated to ¾th. The residue was extracted with EtOAc (3×50 ml) and washed with aq. sat. NaCl. The organics were combined, dried over MgSO4 and concentrated to give (1Z,2Z)-2-{[(2-amino-1,3-thiazol-4-yl)methoxy]imino}-N′-hydroxy-2-phenylethanimidamide (5.86 g) as a white solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09090600B2uspto-grants-2015_07