Sodium Azide → HCID 86749742, compound

HRID 1940648Notes

Reaction equation

HRID 1940648 reaction equation
CS(O[CH2:6][C@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[C:15]([F:32])[CH:14]=2)[CH2:8]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:33]([CH2:6][C@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH2:20]3)=[C:15]([F:32])[CH:14]=2)[CH2:8]1)=[N+:34]=[N-:35]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86749741HCID 86749741, compound

Product 1

HCID 86749742HCID 86749742, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A solution of the 16.8 g(35.5 mmol) of the mesylate 3 in 400 mL of dimethylformamide was treated with 11.5 g(177.5 mmol) of sodium azide followed by warming at 60° C. for 16 h. The solution was diluted with ethyl acetate and extracted with water. The organic layer was dried (Na2SO4) and concentrated in vacuo to afford 14.9 g(100%) of the azide 4 as a light yellow solid, mp 101°-104° C., sufficiently pure for further use.

Workup

  1. extractionextracted with water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2be9268572b441ba6977747854b5571
Source dataset
uspto-grants-1997_12
Patent number
US05700799

Reaction notes

Loading…