Benzenesulfonamide → Cyclohexylurea

HRID 2163217Notes

Reaction equation

HRID 2163217 reaction equation
C1(S([NH2:10])(=O)=O)C=CC=CC=1.NCCC1C=CC(S(N)(=O)=O)=CC=1.CN1C=CC=C(C(O)=O)C1=O.C(=O)([O-])[O-].[K+].[K+].[CH:41]1([N:47]=[C:48]=[O:49])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1>CC(C)=O>[CH:41]1([NH:47][C:48](=[O:49])[NH2:10])[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1

Participants

7

Reactant 5

HCID 7370BenzenesulfonamideHCID 11430Potassium CarbonateHCID 18502Cyclohexyl isocyanateHCID 1696824-(2-Aminoethyl)benzenesulfonamideHCID 12015101-Methyl-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 69684Cyclohexylurea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

2.9 g of 4-(β-<1,2-dihydro-1-methyl-2-oxo-nicotinamido>-ethyl)-benzenesulfonamide (melting point 235 - 237° C, prepared from 4-(β-aminoethyl)-benzenesulfonamide and the mixed anhydride of 1,2-dihydro-1-methyl-2-oxo-nicotinic acid in dilute acetone) in 100 ml acetone/100 ml dioxane were refluxed for 3 hours while stirring together with 2.5 g of pulverized potassium carbonate. 1.4 g of cyclohexyl-isocyanate were then added and the mixture was stirred for 8 hours at boiling temperature. The solvent was distilled off under reduced pressure, water was added to the residue, the whole was filtered, the filtrate acidified, the reaction product was filtered off with suction and recrystallized from dilute ethanol. The N-[4-(β-<1,2 -dihydro-1-methyl-2-oxo-nicotinamido>-ethyl)-benzenesulfonyl]N'-cyclohexyl urea obtained melted at 210 - 212° C.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, water
  2. additionwas added to the residue
  3. filtrationthe whole was filtered
  4. filtrationthe reaction product was filtered off with suction
  5. customrecrystallized from dilute ethanol

Sources & evidence

ORD record
ord-4073cb45e1454c76a062d8bbc5c7e167
Source dataset
uspto-grants-1979_01
Patent number
US04132795

Reaction notes

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