Benzenesulfonamide → Cyclohexylurea

HRID 2163219Notes

Reaction equation

HRID 2163219 reaction equation
C[O:2][C:3](=O)[NH:4]S(C1C=CC=CC=1)(=O)=O.C1(S(N)(=O)=O)C=CC=CC=1.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCOCC1>[CH:25]1([NH:31][C:3](=[O:2])[NH2:4])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 7965CyclohexylamineHCID 676519Methyl N-(phenylsulfonyl)carbamate

Product 1

HCID 69684Cyclohexylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.0 g of 4-(β<1-ethyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonyl carbamic acid methyl ester (melting point 160 - 161° C, prepared from 4-(β-<1-ethyl-1,2-dihydro-2-oxo-nicotinamido]-ethyl)-benzenesulfonamide and chlorofomic acid methyl ester) in 30 ml of dioxane were gently boiled for 2 hours together with 0.5 g of cyclohexyl amine in a vessel with descending condenser. The solvent was then concentrated under reduced pressure, the residue was dissolved in dilute ammonia and precipitated with dilute hydrochloric acid, the reaction mixture was filtered with suction and the precipitate recrystallized from methanol. The N-[4-(β-<1-ethyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl urea obtained melted at 189 - 190° C.

Workup

  1. concentrationThe solvent was then concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dilute ammonia
  3. customprecipitated with dilute hydrochloric acid
  4. filtrationthe reaction mixture was filtered with suction
  5. customthe precipitate recrystallized from methanol

Sources & evidence

ORD record
ord-4d9351cf56284838904e075cdb69f1c7
Source dataset
uspto-grants-1979_01
Patent number
US04132795

Reaction notes

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