Phenyl isocyanate → HCID 21513119, compound

HRID 1576000Notes

Reaction equation

HRID 1576000 reaction equation
C(OCC)(=O)C.[OH:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[NH:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14].[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(N(CC)CC)C>[C:20]1([NH:26][C:27]([O:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[NH:11][C:12](=[O:16])[C:13]([CH3:15])=[CH2:14])=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 21225962HCID 21225962, compound

Product 1

HCID 21513119HCID 21513119, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

A reaction vessel is charged with 100 parts of ethyl acetate and 17.7 parts of 3'-hydroxy-2-methylacrylanilide and heated with stirring to about 65°C. Phenyl isocyanate, 12 parts, is added. No apparent reaction occurs until one part of triethylamine is added to the reaction mixture. After a slight exothermic increase in temperature, the reaction mixture is heated at reflux for one-half hour, cooled and filtered. The solids are washed with ethyl acetate and air dried to give 22.8 parts of 3'-(phenylcarbamoyloxy)-2-methylacrylanilide, m.p. 177°-178°C.

Workup

  1. temperatureheated
  2. customNo apparent reaction
  3. additionis added to the reaction mixture
  4. temperatureAfter a slight exothermic increase in temperature
  5. temperaturethe reaction mixture is heated
  6. temperatureat reflux for one-half hour
  7. temperaturecooled
  8. filtrationfiltered
  9. washThe solids are washed with ethyl acetate and air
  10. customdried

Sources & evidence

ORD record
ord-96f7fc15b9aa4095944981db02d0eae5
Source dataset
uspto-grants-1976_09
Patent number
US03979202

Reaction notes

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