Sodium Azide → HCID 23369756, compound

HRID 1900857Notes

Reaction equation

HRID 1900857 reaction equation
Br[CH2:2][CH:3]1[O:20][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:21])[NH:11][C:10](=[O:16])[C:9]([CH:17]([CH3:19])[CH3:18])=[CH:8]3.[N-:22]=[N+:23]=[N-:24].[Na+].C(OCC)(=O)C.O>CN(C)C=O>[N:22]([CH2:2][CH:3]1[O:20][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH:4]1[CH3:21])[NH:11][C:10](=[O:16])[C:9]([CH:17]([CH3:19])[CH3:18])=[CH:8]3)=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 22728543Water ethylacetateHCID 23369688HCID 23369688, compound

Product 1

HCID 23369756HCID 23369756, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

The compound obtained in Example 327 (1.97 g, 5.62 mmol) was dissolved in dimethylformamide (25 ml). To the resultant solution, sodium azide (2.2 g, 33.84 mmol) was added, and the mixture was stirred at 150° C. for 3 hours. After the mixture was cooled, ethyl acetate-water was added for phase separation. The organic phase was washed with water, and saturated aqueous sodium chloride solution in this order, and dried. The solvent was distilled off under reduced pressure, and the residue was washed with hexane. 1.3 g of the title compound was obtained (78%).

Workup

  1. temperatureAfter the mixture was cooled
  2. washThe organic phase was washed with water, and saturated aqueous sodium chloride solution in this order
  3. customdried
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-2575c2a30a76443daa499b2faf001938
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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