Urea → Ethyl N-phenylcarbamate

HRID 1388219Notes

Reaction equation

HRID 1388219 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(NC(NC2C=CC=CC=2)=O)C=CC=CC=1.NC(N)=O.[C:28](=[O:33])([O:30][CH2:31][CH3:32])N>C(O)C>[CH2:31]([O:30][C:28](=[O:33])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:32]

Participants

6

Reactant 4

HCID 1176UreaHCID 5641Carbamic acid, ethyl esterHCID 6115AnilineHCID 7595Carbanilide

Product 1

HCID 7591Ethyl N-phenylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the procedure of Example 1, 745 g of aniline, 849 g of N,N'-diphenyl urea, 480 g of urea, 356 g of ethyl carbamate and 1350 g of ethanol (approximately 96%) were reacted for 5.5 hours at 200° C. in the pressure apparatus described in Example 1. After cooling and venting of the apparatus, the reaction mixture was removed, filtered and subjected to fractional distillation. After the excess alcohol had been separated (at normal pressure), the remaining fraction was subjected to distillation at 0.2 mbar. 1934 g (73.2% of the theoretical yield) of N-phenyl carbamic acid ethyl ester melting at from 49° to 51° C. were produced.

Workup

  1. customwere reacted for 5.5 hours at 200° C. in the pressure apparatus
  2. temperatureAfter cooling
  3. customthe reaction mixture was removed
  4. filtrationfiltered
  5. distillationsubjected to fractional distillation
  6. customAfter the excess alcohol had been separated (at normal pressure)
  7. distillationthe remaining fraction was subjected to distillation at 0.2 mbar

Sources & evidence

ORD record
ord-899005a5d3ff4d1dbdd8750d81a4d8ac
Source dataset
uspto-grants-1984_02
Patent number
US04430505

Reaction notes

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