تفاعل #10076

معادلة التفاعل

4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione

(chlorocarbonyl)methyl acetate

→

product

المردود 75.0%

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

المردود 75.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux for 18 hours
3. 3
   أخرىThe solvent was evaporated in vacuo
4. 4
   ترشيحfiltered

الإجراء التجريبي

To a stirred suspension of 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (0.55 g, 2.0 mmol) in THF (30 ml) was added (chlorocarbonyl)methyl acetate (0.55 g, 4.0 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo and the resulting solid was slurried in diethyl ether (20 ml) and filtered to give 0.56 g (75%) of product as an off-white solid: mp 234–236° C.; 1H NMR (DMSO-d6) δ 11.15 (s, 1H), 10.06 (s, 1H), 8.55 (d, J=8.3 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.65 (d, J=7.2 Hz, 1H), 5.17 (dd, J=5.0 and 12.4 Hz, 1H), 4.78 (s, 2H), 2.99–2.85 (m, 1H), 2.65–2.52 (m, 2H), 2.22 (s, 2H), 2.11–2.07 (m, 1H); 13C NMR (DMSO-d6) δ 172.70, 169.69, 169.50, 167.99, 166.57, 136.40, 135.59, 131.35, 125.34, 118.72, 116.96, 62.60, 48.98, 30.90, 21.91, 20.41; Anal. Calcd. For C17H15N3O7: C, 54.69; H, 4.05; N, 11.26. Found: C, 54.43; H, 4.05; N, 10.97.

المصدر