HCID 86239153, compound → HCID 69307219, compound

HRID 2055750Notes

Reaction equation

HRID 2055750 reaction equation
[CH2:1]([O:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:20]=1)[CH2:14][N:15]=[N+]=[N-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[H][H]>CO.CCOCC>[CH2:22]([O:21][C:19]1[CH:18]=[C:13]([CH:12]=[C:11]([O:10][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:20]=1)[CH2:14][NH2:15])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 86239153HCID 86239153, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69307219HCID 69307219, compoundYield 62.26%

Reagents, catalysts & solvents 1

HCID 21864698Diethyl ether methanolSolvent

Procedure

A thick walled glass bottle containing a stir bar was flushed with nitrogen gas. 5% Palladium on activated carbon (0.53 g, 10% by mass) was added and wetted with a solution of 50% methanol/ether (about 10 mL). A solution of 3,5-dinonoxybenzylazide (5.3 g, 12.68 mmol) in 50% methanol/ether (about 40 mL) was added. The mixture was hydrogenated with hydrogen gas at 40 psi for approximately 1 hour. The mixture was then filtered through celite with a controlled vacuum using.50% methanol/ether. The solvent was removed from the filtrate under reduced pressure and then the trace solvent was removed with using high vacuum. The starting material was still present in the resulting organic oil, so hydrogenation and celite filtration were repeated until there is no azide remained (3 times). There was a 7.3 g yield or a 62.26% yield of the derivative. The NMR characterization data for this derivative is as follows. 1NMR (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), 3.78 (s, 2H,), 3.95 (t, J=6.6, 4H,), 6.33 (t, J=2.2, 1H, ArH), 6.44 (d, J=2.2, 2H, ArH).

Workup

  1. additionA thick walled glass bottle containing a stir bar
  2. customwas flushed with nitrogen gas
  3. addition5% Palladium on activated carbon (0.53 g, 10% by mass) was added
  4. filtrationThe mixture was then filtered through celite with a controlled vacuum
  5. customThe solvent was removed from the filtrate under reduced pressure
  6. customthe trace solvent was removed
  7. filtrationso hydrogenation and celite filtration
  8. customyield

Sources & evidence

ORD record
ord-337f8dea07c04b619508f47a0ed5f000
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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