Carbamic acid, ethyl ester → Ethyl N-phenylcarbamate

HRID 2166654Notes

Reaction equation

HRID 2166654 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](=[O:13])([O:10][CH2:11][CH3:12])N>C(O)C>[CH2:11]([O:10][C:8](=[O:13])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:12]

Participants

4

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 6115Aniline

Product 1

HCID 7591Ethyl N-phenylcarbamateYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1024 g aniline, 980 g ethyl carbamate and 1060 g ethanol (approximately 96%) were reacted in the apparatus described in Example 1 for 6.0 hours at 200° C. When the apparatus had cooled and the pressure had been reduced, the reaction mixture was removed, filtered and distilled to remove the excess ethanol. The product was then fractionally distilled at 0.4 m bar. 1373 g N-phenyl-carbamic acid ethyl ester (75.5% of the theoretical yield), were collected and crystallized. The product had a melting point of 51° to 52° C.

Workup

  1. temperatureWhen the apparatus had cooled
  2. customthe reaction mixture was removed
  3. filtrationfiltered
  4. distillationdistilled
  5. customto remove the excess ethanol
  6. distillationThe product was then fractionally distilled at 0.4 m bar

Sources & evidence

ORD record
ord-1ea31ed33da746ecb0bbf42e578688f5
Source dataset
uspto-grants-1983_06
Patent number
US04388238

Reaction notes

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