Sodium Iodide → 2-azido-N-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]methyl]acetamide

HRID 9968

Reaktionsgleichung

Reaktionsgleichung von HRID 9968
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:25])[N:10]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24])[C:11]2=[O:16])=[O:4].[N-:26]=[N+:27]=[N-:28].[Na+].[I-].[Na+]>CC(C)=O>[N:26]([CH2:2][C:3]([NH:5][CH2:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:25])[N:10]([CH:17]1[CH2:22][CH2:21][C:20](=[O:23])[NH:19][C:18]1=[O:24])[C:11]2=[O:16])=[O:4])=[N+:27]=[N-:28]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 10270102TNF-alpha-IN-1

Produkt 1

HCID 101096912-azido-N-[[2-(2,6-dioxo-3-piperidyl)-1,3-dioxo-isoindolin-4-yl]methyl]acetamideAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperaturewas refluxed for 17 hours
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc (60 ml)
  4. washThe EtOAc solution was washed with H2O (30 ml), brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7fef32c3685e4b6683f832c20f4ac0ba
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091353B2

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