Water → Cyclohexylurea

HRID 2163218Notes

Reaction equation

HRID 2163218 reaction equation
C1(S([NH2:10])(=O)=O)C=CC=CC=1.[OH-].[Na+].[CH:13]1([N:19]=[C:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>CC(C)=O>[CH:13]1([NH:19][C:20](=[O:21])[NH2:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 7370BenzenesulfonamideHCID 14798Sodium HydroxideHCID 18502Cyclohexyl isocyanate

Product 1

HCID 69684Cyclohexylurea

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
0 °C

Procedure

6.0 g of 4-(β-<1-ethyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonamide (melting point 215 - 216° C, prepared from 4-(β-aminoethyl)-benzenesulfonamide and 1-ethyl-1,2-dihydro-2-oxo-nicotinic acid chloride) were suspended in 60 ml acetone. After the addition of 8.55 ml 2N sodium hydroxide solution, the reaction mixture was cooled to 0° C, 2.35 g of cyclohexyl isocyanate in 5 ml acetone were added dropwise while stirring and stirring was continued for 1 hour at 0° C and for 4 hours at room temperature. The volume of the reaction mixture was then doubled by adding water, the mixture was filtered and the filtrate acidified with 2N hydrochloric acid. The precipitate was dissolved in dilute ammonia solution and precipitated again with dilute hydrochloric acid, stirred with sodium bicarbonate solution and recrystallized from methanol. The N-[4-(β-<1-ethyl-1,2-dihydro-2-oxo-nicotinamido>-ethyl)-benzenesulfonyl]-N'-cyclohexyl urea obtained in this manner melted at 189 - 190° C.

Workup

  1. stirringstirring
  2. filtrationthe mixture was filtered
  3. dissolutionThe precipitate was dissolved in dilute ammonia solution
  4. customprecipitated again with dilute hydrochloric acid
  5. stirringstirred with sodium bicarbonate solution
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-ee31155489224fa7bb540ffecb0f609b
Source dataset
uspto-grants-1979_01
Patent number
US04132795

Reaction notes

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