반응 #10064

반응 방정식

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

수율 90.8%

용매

acetone

반응 조건

후처리

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

실험 절차

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).

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