4-Chlorophenyl Isocyanate → N-(4-chlorophenyl)-N'-cyclohexanesulfonylurea

HRID 1586852

Reaction equation

HRID 1586852 reaction equation
[CH:1]1([S:7]([NH2:10])(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]=[O:22])=[CH:16][CH:15]=1>CC(C)=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:10][S:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:9])=[O:8])=[O:22])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 75536Cyclohexanesulfonamide

Product 1

HCID 22131300N-(4-chlorophenyl)-N'-cyclohexanesulfonylureaYield 70.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

The general method of procedure A was followed with cyclohexanesulfonamide (1.89 g), acetone (5 ml), 1N sodium hydroxide (11.6 ml). After stirring overnight at room temperature, the mixture was cooled in an ice bath and 4-chlorophenyl isocyanate (1.89 g) dissolved in acetone (5 ml) was added. The mixture was warmed to room temperature and stirred two days, filtered, and the separated white solid washed with water. The filtrates were combined and treated with glacial acetic acid (1 ml) followed by addition of water. The resulting solid was collected by filtration, washed with water and air dried to provide 2.57 g of a tan powder.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. additionwas added
  3. temperatureThe mixture was warmed to room temperature
  4. stirringstirred two days
  5. filtrationfiltered
  6. washthe separated white solid washed with water
  7. additiontreated with glacial acetic acid (1 ml)
  8. additionfollowed by addition of water
  9. filtrationThe resulting solid was collected by filtration
  10. washwashed with water and air
  11. customdried

Sources & evidence

ORD record
ord-5bb114658b344e489df75f7d16931279
Source dataset
uspto-grants-1993_06
Patent number
US05216026

Linked notes

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