Dichloromethane → HCID 69306610, compound

HRID 2055759Notes

Reaction equation

HRID 2055759 reaction equation
[CH2:1]([O:12][C:13]1[CH:14]=[C:15]([CH:20]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:22]=1)[CH2:16][N:17]=[N+]=[N-])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].ClCCl.[N-]=[N+]=[N-]>[Pd].CCOCC.CO>[CH2:24]([O:23][C:21]1[CH:20]=[C:15]([CH:14]=[C:13]([O:12][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH:22]=1)[CH2:16][NH2:17])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 33558AzideHCID 86239159HCID 86239159, compound

Product 1

HCID 69306610HCID 69306610, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21864698Diethyl ether methanolSolvent2×

Procedure

Catalytic (5% by mass) palladium on carbon (0.58 g) was placed into a hydrogenation bottle. The bottle was then placed under N2. To the bottle, 50/50 ether methanol (10 mL) was added. 3,5-diundecoxybenzyl azide (5.0 g, 11.2 mmol) was dissolved in 50/50 ether/methanol (60 mL) and transferred to the bottle. The bottle was attached to a hydrogenator with H2 pressure set at 40 psi and left for 1 hour. Thin layer chromatography (dichloromethane/10% hexanes) indicated that the azide was still present. As a result, the bottle was left on a hydrogenator with H2 pressure at 40 psi for an additional 30 minutes. Thin layer chromatography then showed that the starting material was completely consumed. The contents of the bottle were then vacuum filtered over celite. The filtrate was concentrated using rotary evaporation and then placed under high vacuum for 4 or more hours. This produced a 4.4 g yield or a 93.1% yield of the derivative. The NMR characterization data for the derivative is as follows. 1NMR (300 MHz, CDCl3): 0.86 (t, J=6.3, 6H, CH2CH3), 1.25-1.45 (m, 32H, CH2(CH2)8), 1.74 (p, J=6.6, 4H, OCH2CH2), 3.76 (s, 4H, OCH2), 3.90 (t, J=6.6, 2H, ArCH2Cl), 6.32 (t, J=2.2, 1H, ArH), 6.43 (d, J=2.2, 2H, ArH). 13C NMR (75 MHZ, CDCl3): 14.20, 22.78, 26.14, 29.36, 29.42, 29.49, 29.67, 31.99, 46.35, 68.07, 99.86, 105.56, 144.47, 160.59.

Workup

  1. waitAs a result, the bottle was left on a hydrogenator with H2 pressure at 40 psi for an additional 30 minutes
  2. customwas completely consumed
  3. filtrationvacuum filtered over celite
  4. concentrationThe filtrate was concentrated
  5. customevaporation
  6. customThis produced a 4.4 g
  7. customyield

Sources & evidence

ORD record
ord-4812ec17bfc34588aab16d65a593e3f7
Source dataset
uspto-grants-2008_02
Patent number
US07332529B2

Reaction notes

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