Sodium Azide → HCID 86239159, compound

HRID 2055758Notes

Reaction equation

HRID 2055758 reaction equation
[CH2:1]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)[CH2:16]Cl)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[N-:33]=[N+:34]=[N-:35].[Na+]>CN(C=O)C>[CH2:1]([O:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:20]=1)[CH2:16][N:33]=[N+:34]=[N-:35])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 69305966HCID 69305966, compound

Product 1

HCID 86239159HCID 86239159, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-diundecoxybenzyl chloride (13.5 g, 30.1 mmol) was dissolved in DMF (50 mL) in a 250 mL RBF. Sodium azide (3.94 g, 60.2 mmol) and a magnetic stir bar were added to the RBF. A heating mantel was used to gently heat the reaction mixture. After 1 hour, thin layer chromatography indicated that no starting material was present. The contents of the RBF were transferred to a separatory funnel. Ether (250 mL) and distilled H2O (250 mL) were added to the funnel. The aqueous layer was washed 2 times with ether (250 mL). The ether layers were combined and washed 2 times with saturated ammonium chloride solution (125 mL) and once with saturated sodium chloride solution (125 mL). The ether layer was then dried with magnesium sulfate, gravity filtered and concentrated using rotary evaporation. The resulting light yellow oil was then placed under high vacuum where it solidified. This produced a 13.3 g yield or a 97.1% yield of the derivative. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.88 (t, J=6.3, 6H, CH2CH3), 1.21-1.44 (m, 32H, CH2(CH2)7), 1.77 (p, J=6.6, 4H, OCH2CH2), 3.93 (t, J=6.6, 4H, OCH2), 4.24 (s, 2H, ArCH2Cl), 6.41-6.43 (m, 2H, ArH). 13C NMR (75 MHZ, CDCl3): 14.22, 22.79, 26.13, 29.33, 29.44, 29.49, 29.68, 32.00, 55.00, 68.16, 101.07, 106.50, 137.45, 160.68.

Workup

  1. temperatureto gently heat the reaction mixture
  2. customThe contents of the RBF were transferred to a separatory funnel
  3. distillationEther (250 mL) and distilled H2O (250 mL)
  4. additionwere added to the funnel
  5. washThe aqueous layer was washed 2 times with ether (250 mL)
  6. washwashed 2 times with saturated ammonium chloride solution (125 mL)
  7. dry with materialThe ether layer was then dried with magnesium sulfate, gravity
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customevaporation
  11. customThis produced a 13.3 g
  12. customyield

Sources & evidence

ORD record
ord-ba47cdac949b41d5824ee4d84e523d03
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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