Sodium Azide → HCID 11722646, compound

HRID 2255406Notes

Reaction equation

HRID 2255406 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]([C:9]1[C:14]([OH:15])=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=[C:11]([C:20](=[O:24])[CH:21](Br)[CH3:22])[N:10]=1)([CH3:8])[CH3:7]>O.CC(C)=O>[N:1]([CH:21]([CH3:22])[C:20]([C:11]1[N:10]=[C:9]([C:6]([CH3:5])([CH3:8])[CH3:7])[C:14]([OH:15])=[C:13]([C:16]([CH3:19])([CH3:18])[CH3:17])[N:12]=1)=[O:24])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10043058HCID 10043058, compound

Product 1

HCID 11722646HCID 11722646, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A solution of 1.2 g (18 mmol) of sodium azide in 9.0 mL of water was added dropwise to a solution of 5.5 g (16 mmol) of 1-[4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-2-bromo-1-propanone in 35 mL of acetone. The mixture was stirred for 2 hours then added to 100 mL of water and extracted with ethyl acetate. The organic layers were washed with brine, dried (anhydrous sodium sulfate), and evaporated to yield 4.7 g (96%) of the azide product, mp 91° C.-92° C., suitable for further synthesis.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layers were washed with brine
  3. dry with materialdried (anhydrous sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-ed73fde6130242c2b45635492299155b
Source dataset
uspto-grants-1993_08
Patent number
US05240929

Reaction notes

Loading…