p-Aminocinnamic acid → (E)-3-(4-Ureidophenyl)acrylic acid

HRID 1637882Notes

Reaction equation

HRID 1637882 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[N-:13]=[C:14]=[O:15].[K+]>O.C(O)(=O)C>[NH:1]([C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1)[C:14]([NH2:13])=[O:15]

Participants

5

Reactant 2

HCID 1549514p-Aminocinnamic acidHCID 11051572Potassio isocyanate

Product 1

HCID 18363098(E)-3-(4-Ureidophenyl)acrylic acidYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of (E)-3-(4-aminophenyl)acrylic acid (1.0 g, 5.0 mmol) and potassium isocyanate (2.0 g, 5 equiv.) in a mixture of water and acetic acid (50 mL) was heated at 100° C. for 12 hours. After cooling, a white solid precipitated out. Filtration, washing of the filter cake with a mixture of water and MeOH, and drying it in vacuo gave the title compound (0.82 g, 80%) as a white solid. MP>350° C.

Workup

  1. temperatureAfter cooling
  2. customa white solid precipitated out
  3. filtrationFiltration
  4. washwashing of the filter cake with a mixture of water and MeOH
  5. customdrying it in vacuo

Sources & evidence

ORD record
ord-a15c8252053e4c3da92e096a753245f9
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

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