Azobisisobutyronitrile → 11-(acryloylamino)undecanoic acid

HRID 2088240Notes

Reaction equation

HRID 2088240 reaction equation
[C:1]([O-:6])(=[O:5])[C:2](C)=[CH2:3].C[CH:8]([NH:20][CH3:21])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]2OCCO[C:12]=2[CH:11]=1.C(O)CCC[OH:26].CC(N=N[C:35]([C:38]#N)(C)C)(C#N)C>O.C(O)CC>[C:21]([NH:20][CH2:8][CH2:9][CH2:10][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:3][CH2:2][C:1]([OH:6])=[O:5])(=[O:26])[CH:35]=[CH2:38]

Participants

7

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 80641,4-ButanediolHCID 87595MethacrylateHCID 24257269Ethylenedioxymethylamphetamine

Product 1

HCID 23517111-(acryloylamino)undecanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

For the preparation of stationary phases, the inner walls of capillaries were vinylized with 3-(trimethoxylsilyppropyl methacrylate. Subsequently, AAUA, EDMA, 1-propanol, 1,4-butanediol, water, and AIBN were mixed ultrasonically into a homogenous solution and purged with nitrogen for 10 min. A 45 cm long silanized capillary was tilled with the polymerization mixture up to a length of 35 cm, sealed with rubber septum, and then placed in a gas chromatography (GC) oven to polymerize for 20 hours at 60° C. The reaction scheme for the polymerization is shown in Scheme 1. Each column of the experimental design was made in duplicate. After the polymerization of the mixture, the monolithic column was washed with methanol for 12 hours using a HPLC pump to remove unreacted monomers and porogens. An on-column detection window was made next to the polymer bed using a thermal wire stripper. Finally, the column was cut to 45 cm with an effective length of 30 cm.

Workup

  1. customFor the preparation of stationary phases
  2. custompurged with nitrogen for 10 min
  3. customsealed with rubber septum
  4. customto polymerize for 20 hours at 60° C
  5. customThe reaction scheme for the polymerization
  6. customAfter the polymerization of the mixture
  7. washthe monolithic column was washed with methanol for 12 hours
  8. customto remove unreacted monomers and porogens

Sources & evidence

ORD record
ord-30bcf309d103495b8e0eac70c448f4d9
Source dataset
uspto-grants-2013_05
Patent number
US08435410B2

Reaction notes

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