Sodium Azide → HCID 86239166, compound

HRID 2055763Notes

Reaction equation

HRID 2055763 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>[CH2:5]([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][CH2:32][CH2:8][CH2:9][CH3:10])[CH:22]=1)[CH2:18][N:1]=[N+:2]=[N-:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 69306580HCID 69306580, compound

Product 1

HCID 86239166HCID 86239166, compoundYield 80%

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 the touch, allowed too cool to room temperature, then heated again, (repeated 4 times). The mixture was then washed in a separatory funnel with 500 mL distilled water and ether (4 times with 100 mL). The combined ether layers were washed with ammonium chloride (2 times with 50 mL), and then the ether layer was dried with magnesium sulfate and gravity filtered into a 1 L RBF. Thin layer chromatography (10% dichlormethane/hexanes) analysis revealed that there was still a starting material in the product so the product was purified by silica gel flash chromatography (2 L 5% dichloromethane and hexanes, 2 L 7% dichloromethane and hexanes). The solvent was removed under reduced pressure and the trace solvent was removed with high vacuum. There was a 5.3 g yield or a 80% yield. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.87 (t, J=6.6, 6H, CH2CH3), 1.15-1.6 (m, 36H, CH2(CH2)9), 1.76 (p, J=8.0, 4H, OCH2CH2), 3.93 (t, J=6.3, 4H, OCH2CH2), 4.24 (s, 2H, ArCH2), 6.41 (d, J=2.2, 3H, ArH).

Workup

  1. customThe reaction mixture was then capped with a septum
  2. temperatureThe mixture was heated
  3. temperatureuntil warm to the touch
  4. temperatureheated again
  5. washThe mixture was then washed in a separatory funnel with 500 mL
  6. distillationdistilled water and ether (4 times with 100 mL)
  7. washThe combined ether layers were washed with ammonium chloride (2 times with 50 mL)
  8. dry with materialthe ether layer was dried with magnesium sulfate and gravity
  9. filtrationfiltered into a 1 L RBF
  10. customwas purified by silica gel flash chromatography (2 L 5% dichloromethane and hexanes, 2 L 7% dichloromethane and hexanes)
  11. customThe solvent was removed under reduced pressure
  12. customthe trace solvent was removed with high vacuum
  13. customyield

Sources & evidence

ORD record
ord-2c887d0ce3d24285bbe3aaec63f465ed
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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