Pyridine → N-(2,4,6-trimethoxyphenyl)-N'-(4-isopropylcyclohexyl)urea

HRID 37293Notes

Reaction equation

HRID 37293 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([N:10]=[C:11]=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[CH3:13][O:14][C:15]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:24][CH3:25])[C:16]=1[NH2:17].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:25][O:24][C:18]1[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=[C:15]([O:14][CH3:13])[C:16]=1[NH:17][C:11]([NH:10][CH:7]1[CH2:8][CH2:9][CH:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]1)=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 842712,4,6-TrimethoxyanilineHCID 199351384-Isopropylcyclohexylisocyanate

Product 1

HCID 19935028N-(2,4,6-trimethoxyphenyl)-N'-(4-isopropylcyclohexyl)urea

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.6 g of 4-isopropylcyclohexylisocyanate in chloroform is added a solution of 1.8 g of 2,4,6-trimethoxyaniline in chloroform dropwise in the presence of pyridine. The mixture is stirred at room temperature until starting compounds disappear on TLC. The resultant mixture is concentrated and the residue is dissolved in ethyl acetate. The solution is washed with diluted hydrochloric acid, aqueous sodium hydrogencarbonate solution and brine. The organic layer is dried over magnesium sulfate and filtered off. The filtrate is distilled away and the resulting residue is crystallized to give N-(2,4,6-trimethoxyphenyl)-N'-(4-isopropylcyclohexyl)urea.

Workup

  1. concentrationThe resultant mixture is concentrated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washThe solution is washed with diluted hydrochloric acid, aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered off
  6. distillationThe filtrate is distilled away
  7. customthe resulting residue is crystallized

Sources & evidence

ORD record
ord-374741eaee854b63a8671fa751bb72c9
Source dataset
uspto-grants-1995_05
Patent number
US05420164

Reaction notes

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