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

HRID 37294Notes

Reaction equation

HRID 37294 reaction equation
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[CH3:13][N:14]([CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:15](Cl)=[O:16]>N1C=CC=CC=1.ClCCl>[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:6]=1[NH:7][C:15]([N:14]([CH3:13])[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 831552-tert-Butyl-6-methylanilineHCID 19935034N-methyl-N-(2-phenylcyclohexyl)carbamoylchloride

Product 1

HCID 19935187N-(2-tert-butyl-6-methylphenyl)-N'-methyl-N'-(2-phenylcyclohexyl)urea

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-01f89205b7bd469b9be2af90e59305c7
Source dataset
uspto-grants-1995_05
Patent number
US05420164

Reaction notes

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