Hydrogen Peroxide → Cyclohexylurea

HRID 2398585Notes

Reaction equation

HRID 2398585 reaction equation
[CH:1]1([NH:7][C:8](=S)[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(S(N)(=O)=[O:18])C=CC=CC=1.C1(N=C=S)CCCCC1.OO>C(=O)([O-])[O-].[K+].[K+].CO.[OH-].[Na+]>[CH:1]1([NH:7][C:8](=[O:18])[NH2:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 7370BenzenesulfonamideHCID 14289Cyclohexyl isothiocyanateHCID 1471603Cyclohexylthiourea

Product 1

HCID 69684Cyclohexylurea

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 11430Potassium CarbonateSolventHCID 14798Sodium HydroxideSolvent

Procedure

5 Grams N-[4-(β-<N'-methyl-N'-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-thio-urea (prepared by reaction of 4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonamide and cyclohexylisothiocyanate in an acetonic solution in the presence of potassium carbonate, melting point 143°-145° C. from methanol) were dissolved in 50 ml of 1N sodium hydroxide solution. 5 Milliliters of 30% H2O2 were added and the mixture was heated for 15 minutes on the steam bath. After cooling the solution was acidified. The precipitate was suction-filtered and recrystallized from ethanol/dimethylformamide. The N'-[4-(β-<N'-methyl-N'-2-pyridyl-ureido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl-urea obtained melted at 167°-169° C.

Workup

  1. temperaturethe mixture was heated for 15 minutes on the steam bath
  2. temperatureAfter cooling the solution
  3. filtrationThe precipitate was suction-filtered
  4. customrecrystallized from ethanol/dimethylformamide

Sources & evidence

ORD record
ord-aa773fd0d65e444f8b3edcfa99ad2b92
Source dataset
uspto-grants-1977_05
Patent number
US04025519

Reaction notes

Loading…