Azobisisobutyronitrile → HCID 178454695, compound

HRID 1982520Notes

Reaction equation

HRID 1982520 reaction equation
[CH:1]1[CH:2]=[CH:3][N+:4]([O-:8])=[C:5]([SH:7])[CH:6]=1.[C:9]([O-:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17].CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)Cl>[CH:1]1[CH:2]=[CH:3][N+:4]([O-:8])=[C:5]([SH:7])[CH:6]=1.[C:9]([O-:14])(=[O:13])[C:10]([CH3:12])=[CH2:11].[C:15]([O:20][CH3:21])(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 178454790HCID 178454790, compound

Product 1

HCID 178454695HCID 178454695, compoundYield 1,395.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 6-ml flask was charged with 0.097 g of pyrithione methacrylate (0.5 mmole), 2.60 ml of methyl methacrylate (24.5 mmole) and 0.083 g of AIBN (0.5 mmole). The flask was sealed and placed in an oven at 80° C. for 16 hours. After cooling to room temperature, the product was diluted with 15 ml of methylene chloride and filtered. The solution was concentrated via roto-evaporation and 2.18 g of the desired product was isolated as a white polymeric material for an 85.5% yield. The structure was confirmed by NMR and IR. Similar results were obtained by employing either acetyl peroxide, benzoyl peroxide, or lauryl peroxide as the radical initiator.

Workup

  1. customThe flask was sealed
  2. filtrationfiltered
  3. concentrationThe solution was concentrated via roto-evaporation

Sources & evidence

ORD record
ord-2b15a70a38984cf48da74715b0e81c60
Source dataset
uspto-grants-1986_06
Patent number
US04596864

Reaction notes

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