Azobisisobutyronitrile → HCID 86743294, compound

HRID 345915Notes

Reaction equation

HRID 345915 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH:3]=[CH:2]1.[CH3:8][C:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH2:17])=[CH:14][CH:13]=1)([CH3:11])[CH3:10].N(C(C)(C)C#N)=NC(C)(C)C#N.C1(=O)CCCCC1>O>[C:4]1(=[O:6])[NH:5][C:1](=[O:7])[CH:2]=[CH:3]1.[CH3:11][C:9]([C:12]1[CH:13]=[CH:14][C:15]([CH:16]=[CH2:17])=[CH:18][CH:19]=1)([CH3:8])[CH3:10]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7967CyclohexanoneHCID 10935MaleimideHCID 156274-tert-Butylstyrene

Product 1

HCID 86743294HCID 86743294, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Thus, 4 g of maleimide, 6.6 g of 4-(2-methyl-2-propyl) styrene (obtained from Polysciences, Inc.), 42 mg of azobisisobutyronitrile and 40 mL of cyclohexanone were mixed and deoxygenated with argon. This solution was heated in a sealed tube at 60° C. for 4 hours. The resulting polymer was isolated by pouring the polymer solution into cold water, filtering, washing and drying under vacuum. The dried polymer (yield 95% of theoretical) had a melting point of greater than 300° C. The 1H NMR spectrum showed 0.7 NH groups for each aryl group. The polymer was soluble in aqueous alkaline solution of pH equal to 13 or higher. The relative viscosity, ηrel, was 1.15 (0.5 g of polymer per deciliter in DMF at 25° C.). As in Example 2 above, a chain transfer agent may be included to control molecular weight.

Workup

  1. customdeoxygenated with argon
  2. customThe resulting polymer was isolated
  3. filtrationfiltering
  4. washwashing
  5. customdrying under vacuum
  6. custom1.15 (0.5 g of polymer per deciliter in DMF at 25° C.)

Sources & evidence

ORD record
ord-df3f7fa0886349a2b9ba6de8f7976a76
Source dataset
uspto-grants-1991_10
Patent number
US05059513

Reaction notes

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