반응 #10108

반응 방정식

(methylthio)acetic acid

oxalyl chloride

DMF

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

→

N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methylsulfanyl-acetamide

수율 69.2%

용매

ether

methanol

THF

반응 조건

후처리

1. 1
   온도Then the mixture was heated
2. 2
   온도to reflux for 15 h
3. 3
   기타to give a suspension
4. 4
   여과The suspension was filtered
5. 5
   세척washed with methanol (10 mL)

실험 절차

To a solution of (methylthio)acetic acid (0.77 mL, 8.9 mmol) and oxalyl chloride (0.7 mL, 8.0 mmol) in ether (5 mL) was added DMF (0.02 mL) at room temperature. After 3 h, 4-amino-2-(2,6-dioxo(3-piperidyl))isoindoline-1,3-dione (1.1 g, 4.0 mmol) and THF (40 mL) was added to the mixture. Then the mixture was heated to reflux for 15 h. To the mixture was added methanol (10 mL) to give a suspension. The suspension was filtered and washed with methanol (10 mL) to give N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-2-methylsulfanyl-acetamide as a white solid (1.0 g, 69% yield): mp, 228–230° C.; 1H NMR (DMSO-d6) δ 2.05–2.10 (m, 1H, CHH), 2.18 (s, 3H, CH3), 2,46–2.65 (m, 2H, CH2), 2.82–2.95 (m, 1H, CHH), 3.53 (s, 2H, CH2), 5.17 (dd, J=5.2, 12.6 Hz, 1H, NCH), 7.63 (d, J=7.2 Hz, 1H, Ar), 7.86 (t, J=7.5 Hz, 1H, Ar), 8.61 (d, J=8.4 Hz, 1H, Ar), 10.39 (s, 1H, NH), 11.16 (s, 1H, NH); 13C NMR (DMSO-d6) δ 15.62, 21.96, 30.93, 37.99, 48.94, 116.69, 118.46, 125.28, 131.44, 136.31, 166.67, 167.88, 168.63, 169.78, 172.75; Anal Calcd for C16H15N3O5S: C, 53.18; H, 4.18; N, 11.63. Found: C, 53.26; H, 4.17; N, 11.52.

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