Benzenesulfonamide → Cyclohexylurea

HRID 2163220Notes

Reaction equation

HRID 2163220 reaction equation
C1(S([NH2:10])(=O)=O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[CH:17]1([N:23]=[C:24]=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CC(C)=O.O1CCOCC1.O>[CH:17]1([NH:23][C:24](=[O:25])[NH2:10])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 3

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 18502Cyclohexyl isocyanate

Product 1

HCID 69684Cyclohexylurea

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

7.6 g of 4-(β-<1-butyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonamide (melting point 162 - 163° C, prepared from 4-(β-aminoethyl)-benzenesulfonamide and 1-butyl-1,2-dihydro-2-oxo-nicotinic acid chloride in chloroform/soda solution) in 100 ml acetone and 50 ml dioxane were refluxed for 3 hours while stirring together with 5.5 g of pulverized potash. 2.5 g cyclohexyl isocyanate were then added and stirring was continued for 6 hours with reflux. After cooling, the reaction mixture was diluted with water, filtered and the filtrate acidified with 2N hydrochloric acid. The formed precipitate was filtered off with suction, dissolved in dilute ammonia and reprecipitated with dilute hydrochloric acid and finally recrystallized from methanol. The N-[4-(β-<1-butyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl benzenesulfonyl]-N'-cyclohexyl urea obtained melted at 178 - 179° C.

Workup

  1. temperaturewith reflux
  2. temperatureAfter cooling
  3. filtrationfiltered
  4. filtrationThe formed precipitate was filtered off with suction
  5. dissolutiondissolved in dilute ammonia
  6. customreprecipitated with dilute hydrochloric acid
  7. customfinally recrystallized from methanol

Sources & evidence

ORD record
ord-54a15a2c1f8949349bc7cb05423a363a
Source dataset
uspto-grants-1979_01
Patent number
US04132795

Reaction notes

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