Reaction #65572

Reaction equation

2-tert-butyl-6-methylaniline

N-methyl-N-(2-phenylcyclohexyl)carbamoylchloride

→

N-(2-tert-butyl-6-methylphenyl)-N'-methyl-N'-(2-phenylcyclohexyl)urea

Solvents

pyridine

dichloromethane

Conditions

Workup

1. 1
   ConcentrationThe mixture is concentrated
2. 2
   workup.DISSOLUTIONthe residue is dissolved in ethyl ether
3. 3
   WashThe solution is washed with diluted hydrochloric acid, aqueous sodium hydrogencarbonate solution and brine
4. 4
   DryingThe organic layer is dried over sodium sulfate
5. 5
   Filtrationfiltered off
6. 6
   workup.DISTILLATIONThe filtrate is distilled away
7. 7
   Otherthe resuling residue is crystallized

Procedure

To a solution of 0.82 g of 2-tert-butyl-6-methylaniline in pyridine is added a solution of 1.2 g of N-methyl-N-(2-phenylcyclohexyl)carbamoylchloride in dichloromethane dropwise. The mixture is stirred at room temperature until starting compounds disappear on TLC. The mixture is concentrated and the residue is dissolved in ethyl ether. The solution is washed with diluted hydrochloric acid, aqueous sodium hydrogencarbonate solution and brine. The organic layer is dried over sodium sulfate and filtered off. The filtrate is distilled away and the resuling residue is crystallized to give N-(2-tert-butyl-6-methylphenyl)-N'-methyl-N'-(2-phenylcyclohexyl)urea.

Source