Sodium Azide → 2-azido-N-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]acetamide

HRID 9987Notes

Reaction equation

HRID 9987 reaction equation
[O:1]=[C:2]1[CH:7]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[NH:18][C:19](=[O:22])[CH2:20]Cl)[C:9]2=[O:23])[CH2:6][CH2:5][C:4](=[O:24])[NH:3]1.[N-:25]=[N+:26]=[N-:27].[Na+]>CC(C)=O>[N:25]([CH2:20][C:19]([NH:18][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:16](=[O:17])[N:8]([CH:7]1[CH2:6][CH2:5][C:4](=[O:24])[NH:3][C:2]1=[O:1])[C:9]2=[O:23])=[O:22])=[N+:26]=[N-:27]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 10154850Acetamide, 2-chloro-N-[2-(2,6-dioxo-3-piperidinyl)-2,3-dihydro-1,3-dioxo-1H-isoindol-4-yl]-

Product 1

HCID 101551822-azido-N-[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]-2-chloroacetamide (1.53 g, 4.4 mmol) in acetone (30 ml) was added sodium azide (0.43 g, 6.6 mmol). The mixture was heated to reflux for 18 hours. The solvent was evaporated in vacuo to give 1.49 g (96%) of product as an off-white solid: 1H NMR (DMSO-d6) δ 11.19 (s, 1H), 10.20 (s, 1H), 8.49 (d, J=8.3 Hz, 1H), 7.88 (t, J=7.7 Hz, 1H), 7.68 (d, J=7.3 Hz, 1H), 5.17(dd, J=5.1 and 12.7 Hz, 1H), 4.34 (s, 2H), 2.99–2.84 (m, 1H), 2.65–2.47 (m, 2H), 2.09–2.00 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hours
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5ff41231fe2d4459a579918e68254db6
Source dataset
uspto-grants-2006_08
Patent number
US07091353B2

Reaction notes

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