Sodium Azide → HCID 15690201, compound

HRID 1835840Notes

Reaction equation

HRID 1835840 reaction equation
[C:1]([N@@:4]1[CH2:6][CH:5]1[CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])(=[O:3])[CH3:2].[N-:14]=[N+:15]=[N-:16].[Na+]>CN(C=O)C.[Cl-].[Cl-].[Zn+2]>[CH2:9]([O:8][CH:7]([O:11][CH2:12][CH3:13])[C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][N:14]=[N+:15]=[N-:16])[CH3:10]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 21894829HCID 21894829, compound

Product 1

HCID 15690201HCID 15690201, compoundYield 62.9%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture containing 3.26 g of 124 and 15 g of sodium azide in 140 ml of DMF was added 140 ml of ZnCl2 (1.0M solution in Et2O). The mixture was stirred at 75° C. for 3 days and then extracted with EtOAc. The organic layer was washed with water, dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (hexane/EtOAc=3:2) to yield 2.52 g of 125 (62%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (hexane/EtOAc=3:2)

Sources & evidence

ORD record
ord-5267013bec4247398448a6636463cd18
Source dataset
uspto-grants-2004_08
Patent number
US06774140B1

Reaction notes

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