Sodium Azide → HCID 86239153, compound

HRID 2055749Notes

Reaction equation

HRID 2055749 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:22]=1)[CH2:18]Cl)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>CN(C=O)C>[CH2:24]([O:23][C:21]1[CH:20]=[C:17]([CH:16]=[C:15]([O:14][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH:22]=1)[CH2:18][N:1]=[N+:2]=[N-:3])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 69306580HCID 69306580, compound

Product 1

HCID 86239153HCID 86239153, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (3.25 g, 50.0 mmol) and DMF (25 mL) were introduced into a 1 L RBF containing 3,5-dinonoxybenzylchloride (10.0 g, 25.0 mmol) and a stir bar. The reaction mixture was then capped with a septum and an out-vent needle. The mixture was heated until warm to touch, allowed to cool to room temperature, then heated again (repeated 4 times). The mixture was then transferred to a separatory funnel and diluted with 500 mL distilled water and washed with ether (4 times using 100 mL). The combined ether layers were washed with ammonium chloride (2 times with 50 mL), then dried with magnesium sulfate and gravity filtered into a 1 L RBF. The solvent was removed under reduced pressure and the trace solvent was removed with a high vacuum. The compound was purified by flash column chormatography (silica gel using 1 L pure hexanes, 1 L 5% ether and hexanes, 1 L 10% ether and hexanes). The product was present in all fractions, the solvent was removed by rotary evaporation and then the trace solvent was removed by a high vacuum. The resulting yellow oil was dissolved in 400 mL ethanol and placed in a freezer overnight. Extreme crystal growth was present in the morning. The mixture was then vacuum filtered and the crystals were collected and air dried while the filtrate was placed in the freezer. Analysis of the crystals indicates they are impurities. As a result, the solvent was removed from the filtrate using rotary evaporation and the trace solvent was then removed using high vacuum. There was a 5.3 g yield or a 51.4% yield of the derivative. The NMR characterization data for this derivative is as follows. 1H NMR (300 MHz, CDCl3): 0.88 (t, J=6.3, 6H, CH2CH3), 1.1-1.55 (m, 28H, CH2(CH2)6), 1.76 (p, J=6.6, 4H, OCH2CH2), 3.93 (t, J=6.6, 4H,), 4.24 (s, 2H,) 6.42 (q, J=2.2, 1H, ArH). 13C (75 MHz, CDCl3): 160.68, 137.45, 106.52, 101.10, 68.19, 55.01, 31.95, 31.02, 29.47, 29.34, 29.31, 26.12, 22.76, 14.20.

Workup

  1. customThe reaction mixture was then capped with a septum
  2. temperatureThe mixture was heated
  3. temperatureuntil warm
  4. temperatureheated again (repeated 4 times)
  5. customThe mixture was then transferred to a separatory funnel
  6. additiondiluted with 500 mL
  7. distillationdistilled water
  8. washwashed with ether (4 times using 100 mL)
  9. washThe combined ether layers were washed with ammonium chloride (2 times with 50 mL)
  10. dry with materialdried with magnesium sulfate and gravity
  11. filtrationfiltered into a 1 L RBF
  12. customThe solvent was removed under reduced pressure
  13. customthe trace solvent was removed with a high vacuum
  14. customThe compound was purified by flash column chormatography (silica gel using 1 L pure hexanes, 1 L 5% ether and hexanes, 1 L 10% ether and hexanes)
  15. customthe solvent was removed by rotary evaporation
  16. customthe trace solvent was removed by a high vacuum
  17. dissolutionThe resulting yellow oil was dissolved in 400 mL ethanol
  18. filtrationvacuum filtered
  19. customthe crystals were collected
  20. customair dried while the filtrate
  21. customAs a result, the solvent was removed from the filtrate
  22. customevaporation
  23. customthe trace solvent was then removed
  24. customyield

Sources & evidence

ORD record
ord-260a0736b673403ebfee69b97734da85
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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