Toluene → N'-(2-chlorocyclohexyl)-urea

HRID 1580322Notes

Reaction equation

HRID 1580322 reaction equation
C1(S([NH:10][C:11](N)=[O:12])(=O)=O)C=CC=CC=1.C1(C)C=CC=CC=1.[Cl:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH2:28]>C(O)(=O)C>[Cl:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[NH:28][C:11](=[O:12])[NH2:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 118791N-(aminocarbonyl)benzenesulphonamideHCID 4188002-Chlorocyclohexan-1-amine

Product 1

HCID 85911145N'-(2-chlorocyclohexyl)-urea

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 10.3 g of of N-[4-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-ethyl)-benzenesulfonyl-urea (melting point 171° -173°C), 300 ml of toluene, 30 ml of glycolmonomethyl-ether, 1.65 g of glacial acetic acid and 3.3 g of 2-chloro-cyclohexylamine are heated under reflux for 5 hours. Then the whole is concentrated in vacuo and the residue is treated with alcohol. The N-[4-(β<2-methoxy-5-chlorobenzamido> -ethyl)-benzenesulfonyl]-N'-(2-chlorocyclohexyl)-urea obtained as crude product melts at 194° -195°C after recrystallization from methanol/dimethylformamide.

Workup

  1. temperatureare heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThen the whole is concentrated in vacuo
  4. additionthe residue is treated with alcohol

Sources & evidence

ORD record
ord-2336f2a4baa044938270d14e125c5e92
Source dataset
uspto-grants-1976_01
Patent number
US03932503

Reaction notes

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