Sodium Azide → HCID 23369753, compound

HRID 1900804Notes

Reaction equation

HRID 1900804 reaction equation
[OH:1][CH:2]([CH:9]1[O:23][C:12]2=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=[C:11]2[CH2:10]1)[NH:17][C:16](=[O:22])[CH:15]=[CH:14]3)[CH2:3]OS(C)(=O)=O.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C)C=O>[N:24]([CH2:3][CH:2]([CH:9]1[O:23][C:12]2=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=[C:11]2[CH2:10]1)[NH:17][C:16](=[O:22])[CH:15]=[CH:14]3)[OH:1])=[N+:25]=[N-:26]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369622HCID 23369622, compound

Product 1

HCID 23369753HCID 23369753, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-(1-Hydroxy-2-methanesulfonyloxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.66 g, 4.90 mmol) was dissolved in dimethylformamide (50 ml). Sodium azide (1.91 g, 29.4 mmol) was added to the mixture, and the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was condensed under reduced pressure, and the residue was extracted from chloroform-water. The organic phase was dried over sodium sulfate, and condensed under reduced pressure. The resultant residue was purified by silica gel column chromatography (eluent=chloroform: methanol=10:1) to obtain 1.19 g of the title compound as pale yellow powdery crystals (85.0%).

Workup

  1. customcondensed under reduced pressure
  2. extractionthe residue was extracted from chloroform-water
  3. dry with materialThe organic phase was dried over sodium sulfate, and condensed under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography (eluent=chloroform: methanol=10:1)

Sources & evidence

ORD record
ord-7a0c20fde6c747638113a25a2e5a038d
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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