Reaktion #10064

Reaktionsgleichung

2-chloro-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide

sodium azide

sodium iodide

→

2-azido-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide

Ausbeute 90.8%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for 17 hours
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (60 ml)
4. 4
   WaschenThe EtOAc solution was washed with H2O (30 ml), brine (30 ml)
5. 5
   Trocknendried (MgSO4)
6. 6
   SonstigeThe solvent was removed in vacuo

Vorschrift

A mixture of 2-chloro-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.3 g, 3.57 mmol), sodium azide (0.3 g, 4.65 mmol) and sodium iodide (0.54 g, 3.57 mmol) in acetone (50 ml) was refluxed for 17 hours. The solvent was removed in vacuo and the residue was dissolved in EtOAc (60 ml). The EtOAc solution was washed with H2O (30 ml), brine (30 ml), and dried (MgSO4). The solvent was removed in vacuo to give 2-azido-N-{[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]methyl}acetamide (1.2 g, 90%) as a white solid: 1H NMR (CDCl3) δ d 8.48 (s, 1H), 7.84–7.68 (m, 3H), 7.51 (t, J=6.3 Hz, 1H), 5.04–4.97 (dd, J=4.7 and 11.8 Hz, 1H), 4.80 (d, J=6.5 Hz, 2H), 3.97 (s, 2H), 2.95–2.74 (m, 3H), 2.20–2.15 (m, 1H).

Quelle