Sodium Azide → HCID 67541521, compound

HRID 444613Notes

Reaction equation

HRID 444613 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[N-:21]=[N+]=[N-].[Na+]>C(#N)C.C1COCC1.C(OCC)(=O)C>[NH2:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 67541192HCID 67541192, compound

Product 1

HCID 67541521HCID 67541521, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound 22 (0.506 g) was dissolved in 50 ml of acetonitrile. Sodium azide (0.395 g) was then added to that, and 29-hour reaction was carried out by refluxing, followed by 95-hour reaction at room temperature. After the resultant was cooled down to room temperature, the solid components were removed by filtration. The solvent of the filtrate was then distilled away under reduced pressure, and 0.313 g of a transparent, viscous liquid was obtained. This liquid was dissolved in 15 ml of THF distilled from calcium hydride in a nitrogen atmosphere, and was cooled in an ice bath. Lithium aluminum hydride (0.054 g) was then dissolved in 20 ml of dried THF, and was dripped. After the resultant was stirred in an ice bath for one hour, 80 μl of ion-exchange water, 80 of 15 wt % of aqueous potassium hydride solution, and 240 μl of ion-exchange water were added so as to stop the reaction. The precipitate generated was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The solid obtained was then dissolved in ethyl acetate (30 ml), and was washed twice with 30 ml of ion-exchange water. The organic phase was then collected, and was dehydrated with magnesium sulfate. The desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. In this manner, 0.2 g of (11-aminoundecyl)tolylether 23, which was a white solid, was obtained.

Workup

  1. custom29-hour reaction
  2. temperatureby refluxing
  3. waitfollowed by 95-hour
  4. customreaction at room temperature
  5. customthe solid components were removed by filtration
  6. distillationThe solvent of the filtrate was then distilled away under reduced pressure, and 0.313 g of a transparent, viscous liquid
  7. customwas obtained
  8. distillationdistilled from calcium hydride in a nitrogen atmosphere
  9. temperaturewas cooled in an ice bath
  10. dissolutionLithium aluminum hydride (0.054 g) was then dissolved in 20 ml of dried THF
  11. addition80 μl of ion-exchange water, 80 of 15 wt % of aqueous potassium hydride solution, and 240 μl of ion-exchange water were added so as
  12. customthe reaction
  13. customThe precipitate generated was removed by filtration
  14. distillationthe solvent of the filtrate was distilled away under reduced pressure
  15. customThe solid obtained
  16. washwas washed twice with 30 ml of ion-exchange water
  17. customThe organic phase was then collected
  18. customThe desiccant agent was removed by filtration
  19. distillationthe solvent of the filtrate was distilled away under reduced pressure
  20. customwas obtained

Sources & evidence

ORD record
ord-c0c17d98387444938fa04de621c89eac
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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