Acetaminophen → N-{4-[(2-Methylprop-2-enoyl)oxy]phenyl}ethanimidic acid

HRID 1420139Notes

Reaction equation

HRID 1420139 reaction equation
C(O)(=O)C=C.[C:6]([OH:11])(=[O:10])[C:7]([CH3:9])=[CH2:8].[CH3:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19](O)=[CH:20][CH:21]=1)=[O:14]>C(Cl)(=O)C(C)=C>[C:6]([O:11][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:13](=[O:14])[CH3:12])=[CH:21][CH:20]=1)(=[O:10])[C:7]([CH3:9])=[CH2:8]

Participants

5

Reactant 3

HCID 1983Acetaminophen2×HCID 4093Methacrylic AcidHCID 6581Acrylic Acid

Product 1

HCID 216863N-{4-[(2-Methylprop-2-enoyl)oxy]phenyl}ethanimidic acid

Reagents, catalysts & solvents 1

HCID 13528Methacryloyl chlorideSolvent

Procedure

In order to obtain the polymeric drug of the present invention, it is firstly required to obtain a monomer of acrylic acid or methacrylic acid derivatives by reacting a low molecular physiological active substance with acrylic acid or methacrylic acid. The above-mentioned monomer may be obtained in the manner as stated below, in case of using acetaminophen, for example. That is, acetaminophen is dissolved in an acetonitrile anhydride, and methacryloyl chloride is added drop by drop to the solution. The resulting reaction solution is stirred for 30 minutes at a room temperature, followed by the removal of a reaction solvent by distillation. The residue is dissolved in chloroform, and dried, followed by recrystallization from benzene to obtain p-methacryloyloxyacetanilide.

Workup

  1. customThe above-mentioned monomer may be obtained in the manner
  2. additionis added drop by drop to the solution
  3. customThe resulting reaction solution
  4. customfollowed by the removal of a reaction solvent by distillation
  5. dissolutionThe residue is dissolved in chloroform
  6. customdried
  7. customfollowed by recrystallization from benzene

Sources & evidence

ORD record
ord-8f540346a8cb4c9696be495df7f685a0
Source dataset
uspto-grants-1999_03
Patent number
US05889078

Reaction notes

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