Azobisisobutyronitrile → HCID 86654956, compound

HRID 1926554Notes

Reaction equation

HRID 1926554 reaction equation
[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:13]([NH2:18])(=[O:17])[C:14]([CH3:16])=[CH2:15].CC(N=NC(C#N)(C)C)(C#N)C>O1CCOCC1>[C:1]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:13]([NH2:18])(=[O:17])[C:14]([CH3:16])=[CH2:15]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 6595MethacrylamideHCID 8872Hexyl methacrylate

Product 1

HCID 86654956HCID 86654956, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9.0 g Hexyl methacrylate, 1.0 g methacrylamide, 80 mg. AIBN, 20 g dioxane, and a stir bar were charged into a 60 mL glass bottle, sealed, and purged with Nitrogen for 30 min. This was put into a 60 degree C. oil bath for 3 hr. The solution was slightly hazy before and after heating, with a small amount of undissolved material at completion. The polymer was precipitated into about 300 mL MeOH, and re-dissolved in about 10 mL DCM. The next two precipitations were done into about 150 mL MeOH, and finally it was dissolved in DCM, and dried on a Teflon sheet. This was first air dried, then put under high vacuum at 40 degrees C. overnight. After drying there was approx. 4 g clear, colorless polymer. The polymer has a glass transition temperature of 29.7° C. and a Mn of 163,589.

Workup

  1. customsealed
  2. custompurged with Nitrogen for 30 min
  3. customThis was put into a 60 degree
  4. temperatureafter heating, with a small amount of undissolved material at completion
  5. customThe polymer was precipitated into about 300 mL MeOH
  6. dissolutionre-dissolved in about 10 mL DCM
  7. customThe next two precipitations
  8. dissolutionwas dissolved in DCM
  9. dry with materialdried on a Teflon sheet
  10. customThis was first air dried
  11. customput under high vacuum at 40 degrees C
  12. customovernight
  13. customAfter drying there was approx. 4 g clear

Sources & evidence

ORD record
ord-572a0691e0c44bd0ae1b0c7687c714f0
Source dataset
uspto-grants-2012_05
Patent number
US08182830B2

Reaction notes

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