Ammonia → Ethyl N-phenylcarbamate

HRID 1633370Notes

Reaction equation

HRID 1633370 reaction equation
C1(N[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])C=CC=CC=1.C(=O)([O:19][CH2:20][CH3:21])N.N>C(O)C>[CH2:20]([O:19][C:8](=[O:9])[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:21]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5641Carbamic acid, ethyl esterHCID 7595Carbanilide

Product 1

HCID 7591Ethyl N-phenylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

637 g of N,N'-diphenyl urea, 267 g of ethyl carbamate and 1880 g of ethanol (approximately 96%) were reacted for 8.5 hours at 200° C. in the pressure apparatus described in Example 1, with the ammonia gas given off being removed. After cooling and venting of the apparatus, the reaction mixture was removed, filtered and subjected to fractional distillation. Excess alcohol was initially distilled off at atmospheric pressure, after which the mixture was distilled off at 0.2 mbar. 766 g (77.3% of the theoretical yield) of N-phenyl carbamic acid ethyl ester which solidified into crystals melting at from 48° to 51° C. were produced.

Workup

  1. custombeing removed
  2. temperatureAfter cooling
  3. customthe reaction mixture was removed
  4. filtrationfiltered
  5. distillationsubjected to fractional distillation
  6. distillationExcess alcohol was initially distilled off at atmospheric pressure
  7. distillationafter which the mixture was distilled off at 0.2 mbar

Sources & evidence

ORD record
ord-b85e9e99bbae4dcf8e55287464351116
Source dataset
uspto-grants-1984_10
Patent number
US04480110

Reaction notes

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