Sodium Azide → HCID 23369667, compound

HRID 1900841Notes

Reaction equation

HRID 1900841 reaction equation
Br[CH2:2][C:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]=1)[NH:11][C:10](=[O:16])[C:9]([CH2:17][CH3:18])=[CH:8]3.[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C)C=O>[N:20]([CH2:2][C:3]1[O:19][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]=1)[NH:11][C:10](=[O:16])[C:9]([CH2:17][CH3:18])=[CH:8]3)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 23369818HCID 23369818, compound

Product 1

HCID 23369667HCID 23369667, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of the compound obtained in Example 308 (3.04 g, 9.45 mmol) in dimethylformamide (150 ml), sodium azide (1.54 g, 26.6 mmol) was added, and the solution was stirred at 120° C. for 100 minutes. The reaction liquid was condensed under reduced pressure, and the residue was extracted from a solvent mixture of chloroform-methanol (4:1). The organic phase was washed with saturated aqueous NaCl solution, dried over sodium sulfate, and condensed under reduced pressure. The resultant residue was recrystallized from chloroform-methanol-hexane. 2.28 g of the title compound was obtained as colorless needles (84.6%).

Workup

  1. customThe reaction liquid
  2. customcondensed under reduced pressure
  3. extractionthe residue was extracted from a solvent mixture of chloroform-methanol (4:1)
  4. washThe organic phase was washed with saturated aqueous NaCl solution
  5. dry with materialdried over sodium sulfate, and condensed under reduced pressure
  6. customThe resultant residue was recrystallized from chloroform-methanol-hexane

Sources & evidence

ORD record
ord-0b8e3147617446d390003a7a6ee52ff8
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

Loading…