Methyl Methacrylate → HCID 178454695, compound

HRID 1982518Notes

Reaction equation

HRID 1982518 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]>C(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[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 2

HCID 6658Methyl MethacrylateHCID 178454790HCID 178454790, compound

Product 1

HCID 178454695HCID 178454695, compoundYield 308.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6344DichloromethaneSolvent

Procedure

A 6-ml flask was charged with 0.487 g of pyrithione methacrylate (2.5 mmole), 2.40 ml of methyl methacrylate (22.5 mmole) and a 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 2.41 g of the desired product was isolated as a yellow polymeric material for a 85.7% 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-2f30f009389747fc9af4f41e904f3903
Source dataset
uspto-grants-1986_06
Patent number
US04596864

Reaction notes

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