Reaction #447173

ord-46709bbc712c497ab10aec2d5d213456

Reaction equation

CCCCc1ccc(CN(CCCCCCOS(C)(=O)=O)C(=O)Nc2c(Cl)cc(Cl)cc2Cl)cc1
1-[(4-butylphenyl)methyl]-1-[6-[(methylsulfonyl)oxy]hexyl]-3-(2,4,6-trichlorophenyl)urea
[Cl-].[K+]
potassium chloride
→
CCCCc1ccc(CN(CCCCCCCl)C(=O)Nc2c(Cl)cc(Cl)cc2Cl)cc1
desired product
Yield 64.7%
CCCCc1ccc(CN(CCCCCCCl)C(=O)Nc2c(Cl)cc(Cl)cc2Cl)cc1
1-[(4-Butylphenyl)methyl]-1-(6-chlorohexyl)-3-(2,4,6-trichlorophenyl)urea
Yield 64.7%

Reactants

CCCCc1ccc(CN(CCCCCCOS(C)(=O)=O)C(=O)Nc2c(Cl)cc(Cl)cc2Cl)cc1
1-[(4-butylphenyl)methyl]-1-[6-[(methylsulfonyl)oxy]hexyl]-3-(2,4,6-trichlorophenyl)urea
[Cl-].[K+]
potassium chloride

Reagents

None

Solvents

CS(C)=O
dimethyl sulfoxide

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewas heated at an oil bath temperature of 60°-70° C. for 20 hours
  2. 2
    ExtractionThe extraction and chromatography procedures of Example 521

Procedure

A mixture of 1.9 g of 1-[(4-butylphenyl)methyl]-1-[6-[(methylsulfonyl)oxy]hexyl]-3-(2,4,6-trichlorophenyl)urea, 0.6 g of potassium chloride, and 3.0 ml of dried dimethyl sulfoxide was heated at an oil bath temperature of 60°-70° C. for 20 hours. The extraction and chromatography procedures of Example 521 were followed to give 1.1 g of the desired product as a colorless oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05003106uspto-grants-1991_03