Toluene → HCID 178454688, compound

HRID 1982521Notes

Reaction equation

HRID 1982521 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](OC)(=O)C(C)=C.[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>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].[CH2:15]=[CH:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 6658Methyl MethacrylateHCID 178454790HCID 178454790, compound

Product 1

HCID 178454688HCID 178454688, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 6344DichloromethaneSolvent

Procedure

A 6-ml flask was charged with 0.489 g of pyrithione methacrylate (2.5 mmole), 2.6 ml of methyl methacrylate (22.5 mmole) and 0.083 g of AIBN (0.5 mmole), and 3 ml of toluene. 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 10 ml of methylene chloride and filtered. The solution was concentrated via roto-evaporation and 2.32 g of the desired product was isolated as a yellow polymeric material for a 79.6% 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-82a6b7f4b1384951b09697d0fffc5790
Source dataset
uspto-grants-1986_06
Patent number
US04596864

Reaction notes

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