Urea → Ethyl N-phenylcarbamate

HRID 1388223Notes

Reaction equation

HRID 1388223 reaction equation
NC(N)=O.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:12](=[O:17])([O:14][CH2:15][CH3:16])N.C([Sn](=O)CCCC)CCC>C(O)C>[CH2:15]([O:14][C:12](=[O:17])[NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:16]

Participants

6

Reactant 4

HCID 1176UreaHCID 5641Carbamic acid, ethyl esterHCID 6115AnilineHCID 61221Dibutyltin oxide

Product 1

HCID 7591Ethyl N-phenylcarbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
170 °C

Procedure

Following the procedure of example 23 60.1 g of urea, 93.1 g of aniline, 8.9 g of ethyl carbamate and 0.5 g of dibutyl-tin-oxide are heated to 170° C. Subsequently 84 g of ethanol are added dropwise at such a rate that the reaction temperature can be maintained between 170° and 175° C. After a total reaction time of 10 hours the reaction is stopped by cooling to room temperature. 161 g (98% of the theoretical yield) of N-phenyl-carbamic acid ethyl ester are found by HPLC analysis.

Workup

  1. temperaturecan be maintained between 170° and 175° C
  2. customAfter a total reaction time of 10 hours
  3. temperatureby cooling to room temperature

Sources & evidence

ORD record
ord-a47699480a7a462395dda761ccef0392
Source dataset
uspto-grants-1984_02
Patent number
US04430505

Reaction notes

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