반응 #10085

반응 방정식

sodium azide

N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]-2-chloroacetamide

NaI

sodium azide

→

product

수율 93.0%

2-azido-N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]acetamide

수율 93.0%

용매

dichloromethane

H2O

acetone

반응 조건

후처리

1. 1
   온도The mixture was heated
2. 2
   온도to reflux for 18 hours
3. 3
   온도The mixture was heated
4. 4
   온도at reflux for an additional 18 hours
5. 5
   기타The solvent was evaporated in vacuo
6. 6
   기타to give an off-white solid which
7. 7
   여과This slurry was filtered

실험 절차

To a stirred suspension of N-[2-(2,6-dioxo(3-piperidyl))-1-oxoisoindolin-4-yl]-2-chloroacetamide (4.64 g, 13.8 mmol) in acetone (60 ml) was added sodium azide (1.35 g, 20.7 mmol). The mixture was heated to reflux for 18 hours. After 18 hours, to the reaction mixture was added NaI (2.05 g, 13.8 mmol) and additional sodium azide (0.90 g, 13.8 mmol). The mixture was heated at reflux for an additional 18 hours. The solvent was evaporated in vacuo to give an off-white solid which was slurried in a mixture of dichloromethane (50 ml) and H2O (50 ml). This slurry was filtered to give 4.39 g (93%) of product: 1H NMR (DMSO-d6) δ 11.50–9.52 (bs, 2H), 7.87–7.84 (m, 1H), 7.59–7.50 (m, 2H), 5.17 (dd, J=5.0 and 13.1 Hz, 1H), 4.44 (d, J=17.6 Hz, 1H), 4.34 (d, J=17.6 Hz, 1H), 4.13 (s, 2H), 3.00–2.86 (m, 1H), 2.65–2.59 (m, 1H), 2.44–2.29 (m, 1H), 2.07–2.02 (m, 1H).

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