反応 #10085

反応方程式

sodium azide

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

NaI

sodium azide

→

product

収率 93.0%

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

収率 93.0%

溶媒

dichloromethane

H2O

acetone

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度to reflux for 18 hours
3. 3
   温度The mixture was heated
4. 4
   温度at reflux for an additional 18 hours
5. 5
   その他The solvent was evaporated in vacuo
6. 6
   その他to give an off-white solid which
7. 7
   ろ過This slurry was filtered

実験手順

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).

出典