Azobisisobutyronitrile → HCID 19795469, compound

HRID 1614682Notes

Reaction equation

HRID 1614682 reaction equation
[C:1]([O:5][CH2:6][CH2:7]CC)(=[O:4])[CH:2]=[CH2:3].C(NCCCNC(=O)[C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28](=[O:30])[CH3:29])=[C:23]([O:31][C:32](=[O:34])[CH3:33])[C:22]=1[O:35][C:36](=[O:38])[CH3:37])(=O)C(C)=C.N(C(C)(C)C#N)=N[C:42](C)(C)C#N.[C:52]([O:55]CC)(=[O:54])C>>[C:1]([O:5][CH2:6][CH2:7][O:55][C:52](=[O:54])[C:26]1[CH:21]=[C:22]([O:35][C:36](=[O:38])[CH3:37])[C:23]([O:31][C:32](=[O:34])[CH3:33])=[C:24]([O:27][C:28](=[O:30])[CH3:29])[CH:25]=1)(=[O:4])[C:2]([CH3:3])=[CH2:42]

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8846Butyl AcrylateHCID 8857Ethyl AcetateHCID 19772431HCID 19772431, compound

Product 1

HCID 19795469HCID 19795469, compound

Conditions

Temperature
60 °C

Procedure

Butyl acrylate (24.4 g, 0.19 mol), and N-(3-(methacrylamido) propyl)-3,4,5-triacetoxybenzamide (IV) (4.20 g, 0.010 mol) were combined with 110 mL ethyl acetate and azobis(isobutyronitrile)(0.16 g) in a vessel sealed with a septum. The vessel was purged with N2 and heated to 60° C. with agitation for 24 h. Additional AIBN (0.16 g) was added and the mixture was heated for an additional 24 h. Yield 124.7 g solution, 22.6% solids. 1H NMR of an evaporated sample showed no residual monomers and was consistent with the desired copolymer structure. Inherent viscosity in ethyl acetate at 25° C., c=0.238 g/dL; ηinh=0.44. The polymer in ethyl acetate solution was then dispersed in a gelatin solution containing surfactant, followed by removal of the ethyl acetate by evaporation before use.

Workup

  1. customsealed with a septum
  2. customThe vessel was purged with N2
  3. additionAdditional AIBN (0.16 g) was added
  4. temperaturethe mixture was heated for an additional 24 h
  5. customat 25° C.
  6. additionThe polymer in ethyl acetate solution was then dispersed in a gelatin solution
  7. additioncontaining surfactant
  8. customfollowed by removal of the ethyl acetate by evaporation before use

Sources & evidence

ORD record
ord-8bb0890b308544c9a8869360a059bb6b
Source dataset
uspto-grants-1993_03
Patent number
US05198517

Reaction notes

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