Ethanol → Carbamic acid, N-(4-chlorophenyl)-, ethyl ester

HRID 1388220Notes

Reaction equation

HRID 1388220 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.NC(N)=O.[C:13](=[O:18])([O:15][CH2:16][CH3:17])N.C(O)C>ClC1C=CC=CC=1>[CH2:16]([O:15][C:13](=[O:18])[NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:17]

Participants

6

Reactant 4

HCID 702EthanolHCID 1176UreaHCID 5641Carbamic acid, ethyl esterHCID 78124-Chloroaniline

Product 1

HCID 17496Carbamic acid, N-(4-chlorophenyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

Following the procedure described in Example 1, 638 g of 4-chloroaniline, 240 g of urea, 89 g of ethyl carbamate, 625 g of ethanol (approximately 96%) and 1400 g of chlorobenzene were reacted for 6.5 hours at 200° C. in the pressure apparatus described in Example 1. After the apparatus had been cooled and vented, the reaction mixture was removed. Excess ethanol was removed by fractional distillation at atmospheric pressure. The mixture (while being stirred) was then exposed to hydrogen chloride gas at room temperature, filtered and subjected to fractional distillation in vacuo. Chlorobenzene was separated off at 15 mbar. Subsequent distillation at 0.2 mbar yielded 785 g (78.6% of the theoretical yield) of N-(4-chlorophenyl)-carbamic acid ethyl ester melting at from 68° to 70° C.

Workup

  1. customwere reacted for 6.5 hours at 200° C. in the pressure apparatus
  2. temperatureAfter the apparatus had been cooled
  3. customthe reaction mixture was removed
  4. customExcess ethanol was removed by fractional distillation at atmospheric pressure
  5. customwas then exposed to hydrogen chloride gas at room temperature
  6. filtrationfiltered
  7. distillationsubjected to fractional distillation in vacuo
  8. customChlorobenzene was separated off at 15 mbar
  9. distillationSubsequent distillation at 0.2 mbar
  10. customyielded 785 g (78.6% of the

Sources & evidence

ORD record
ord-a78cb0d419b8433097db47242d998ae9
Source dataset
uspto-grants-1984_02
Patent number
US04430505

Reaction notes

Loading…