4-Chlorophenyl Isocyanate → N-(4-chlorophenyl)-N'-1-propanesulfonylurea

HRID 1857572Notes

Reaction equation

HRID 1857572 reaction equation
[CH2:1]([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:2][CH3:3].[OH-].[Na+].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>CC(C)=O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:7][S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 3401849Propane-1-sulphonamide

Product 1

HCID 22131290N-(4-chlorophenyl)-N'-1-propanesulfonylureaYield 64.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Procedure A was followed with 1-propanesulfonamide (5.0 g, 40.6 mmole), in acetone (40 ml), and 1.0N sodium hydroxide (40.6 ml). After ten minutes of stirring, 4-chlorophenyl isocyanate (6.2 g, 40.6 mmole) dissolved in about 40 ml of acetone was added over a five minute period. The mixture was allowed to stir for about two hours and filtered. The filtered solid was washed with water which dissolved most of it. 1N HCl (40 ml) was added to the combined filtrates and the resulting precipitate was filtered off and dried at about 65° C. under vacuum to provide 7.2 g of product.

Workup

  1. additionwas added over a five minute period
  2. stirringto stir for about two hours
  3. filtrationfiltered
  4. washThe filtered solid was washed with water which
  5. dissolutiondissolved most of it
  6. addition1N HCl (40 ml) was added to the combined filtrates
  7. filtrationthe resulting precipitate was filtered off
  8. customdried at about 65° C. under vacuum

Sources & evidence

ORD record
ord-aacad6966ed2460f835cab193702c891
Source dataset
uspto-grants-2000_11
Patent number
US06147115

Reaction notes

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