Azobisisobutyronitrile → HCID 86756711, compound

HRID 1978100Notes

Reaction equation

HRID 1978100 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][NH:9][S:10]([C:13]([F:16])([F:15])[F:14])(=[O:12])=[O:11].[C:17]1(=[O:23])[O:22][C:20](=[O:21])[CH:19]=[CH:18]1.CC(N=NC(C#N)(C)C)(C#N)C>O1CCCC1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][NH:9][S:10]([C:13]([F:16])([F:14])[F:15])(=[O:12])=[O:11].[C:20]1(=[O:21])[O:22][C:17](=[O:23])[CH:18]=[CH:19]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 15759318HCID 15759318, compound

Product 1

HCID 86756711HCID 86756711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The N-(bicyclo(2.2.1)hept-5-ene-2-ylmethyl)-1,1,1-trifluoro methanesulfonamide (7.5 g, 30 mmol), Maleic anhydride (2.90 g, 30 mmol), 2,2′-azabisisobutyronitrile (AIBN) (0.40 g, 2.4 mmol) and 30 gr. of dry tetrahydrofuran were placed in a round bottom flask equipped with a water condenser and a firestone valve. The solution was evacuated and purged with nitrogen (4 times) with the aid of the firestone valve. The solution was heated to reflux for 18 hrs. The polymer solution was cooled, diluted with 20 ml of acetone and precipitated dropwise into 800 ml of hexane. The precipitated polymer was separated by decantation, rinsed twice with hexane's and dried under Vacuum (yield 3.3 g). Reprecipitating from acetone into mixtures of hexane/isopropanol (90/10) further purified the isolated polymer. %). The polymer was further characterized using GPC, IR and NMR. The Weight Avg. Mol. Wt of the polymer was observed to be 1,350. The glass transition temperature of the alternating copolymer was found via DSC to be 79° C.

Workup

  1. customequipped with a water condenser and a firestone valve
  2. customThe solution was evacuated
  3. custompurged with nitrogen (4 times) with the aid of the firestone valve
  4. temperatureThe solution was heated
  5. temperatureto reflux for 18 hrs
  6. temperatureThe polymer solution was cooled
  7. additiondiluted with 20 ml of acetone
  8. customprecipitated dropwise into 800 ml of hexane
  9. customThe precipitated polymer was separated by decantation
  10. washrinsed twice with hexane's
  11. customdried under Vacuum (yield 3.3 g)
  12. customReprecipitating from acetone into mixtures of hexane/isopropanol (90/10)
  13. customfurther purified the isolated polymer
  14. customto be 79° C.

Sources & evidence

ORD record
ord-bb8f9e0cfab0402d818f40a124863887
Source dataset
uspto-grants-2001_05
Patent number
US06235849B1

Reaction notes

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