Ammonia → Ethyl N-phenylcarbamate

HRID 1633369

Reaction equation

HRID 1633369 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.NC(N)=O.N.[CH2:22]([OH:24])[CH3:23]>CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.[Zn+2]>[CH2:22]([O:24][C:8](=[O:9])[NH:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:23]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 1176UreaHCID 7595Carbanilide

Product 1

HCID 7591Ethyl N-phenylcarbamate

Reagents, catalysts & solvents 1

HCID 11180Zinc CaprylateCatalyst

Procedure

Following the procedure of Example 1, 573 g of N,N'-diphenyl urea and 2080 g of ethanol (approximately 96%) were reacted for 1.5 hours at 190° C. in the pressure apparatus described in Example 1. After cooling this mixture, 162 g of urea and 5.8 g of zinc octoate were added to the pressure reactor and then reacted for 5.5 hours at 200° C. with removal of the ammonia formed. After cooling and venting of the apparatus, the reaction mixture was removed, filtered and subjected to fractional distillation. Excess alcohol was separated from the reaction mixture at atmospheric pressure. 783 g (87.8% of the theoretical yield) of N-phenyl carbamic acid ethyl ester distilled off at 0.2 mbar. The N-phenyl carbamic acid ethyl ester crystals melted at 49° to 51° C.

Workup

  1. customwere reacted for 1.5 hours at 190° C. in the pressure apparatus
  2. additionwere added to the pressure reactor
  3. customformed
  4. temperatureAfter cooling
  5. customthe reaction mixture was removed
  6. filtrationfiltered
  7. distillationsubjected to fractional distillation
  8. customExcess alcohol was separated from the reaction mixture at atmospheric pressure

Sources & evidence

ORD record
ord-8a4529a6f9a24f6c82e42425340b09e3
Source dataset
uspto-grants-1984_10
Patent number
US04480110

Linked notes

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