Acetone → HCID 19799963, compound

HRID 1646834Notes

Reaction equation

HRID 1646834 reaction equation
[OH:1][C:2]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:3]=1[NH2:4].CC(C)=O.[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17]>COC1C=CC(O)=CC=1.N1C=CC=CC=1>[OH:1][C:2]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:3]=1[NH:4][C:15](=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

6

Reactant 3

HCID 180AcetoneHCID 13528Methacryloyl chlorideHCID 101977194-Amino-3-hydroxybenzonitrile

Product 1

HCID 19799963HCID 19799963, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 1049PyridineSolvent

Procedure

400 g of o-hydroxy-p-cyanoaniline, 4 g of hydroquinone monomethyl ether, 4 litres of acetone, and 360 g of pyridine were mixed and the mixture was cooled externally with a freezing medium. At a point when the internal temperature of the solution had dropped to -10° C., 420 g of methacrylic acid chloride was added dropwise to the mixture with stirring. Thereafter the mixture was treated in the same way as in Synthesis Example 1 to obtain 350 g of o-hydroxy-p-cyanomethacrylanilide. 76.8 g (0.38 mol) of this o-hydroxy-p-cyanomethacrylanilide was dissolved together with 68.4 g (0.60 mol) of ethyl methacrylate, 1.44 g (0.02 mol) of acrylic acid and 0.7 g of α,α'-azobisisobutyronitrile in 300 ml of an acetone/ethanol (1/2) mixed solvent. After replacing the atmosphere with nitrogen gas, the solution was heated at 65° C. for 4 hours to obtain a polymer solution. This polymer solution was poured into 3 litres of aqueous 5% HCl solution and the produced white precipitate was filtered and dried, giving 75 g of a white polymer. Determination of molecular weight of this polymer by the GPC method showed Mn=4,700 and Mw=33,000.

Workup

  1. temperaturethe mixture was cooled externally with a freezing medium
  2. additionAt a point when the internal temperature of the solution had dropped to -10° C.
  3. additionThereafter the mixture was treated in the same way as in Synthesis Example 1

Sources & evidence

ORD record
ord-44a74b43d1fc46f59041922b8d8a3c8b
Source dataset
uspto-grants-1993_01
Patent number
US05182183

Reaction notes

Loading…