Acetone → 1-butylsulfonyl-3-(4-chlorophenyl)urea

HRID 1857574Notes

Reaction equation

HRID 1857574 reaction equation
[Na+].[CH2:2]([S:6]([NH-:9])(=[O:8])=[O:7])[CH2:3][CH2:4][CH3:5].CC(C)=O.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1>O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:9][S:6]([CH2:2][CH2:3][CH2:4][CH3:5])(=[O:8])=[O:7])=[O:23])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 76934-Chlorophenyl IsocyanateHCID 15484971HCID 15484971, compound

Product 1

HCID 2294131-butylsulfonyl-3-(4-chlorophenyl)ureaYield 65.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-butanesulfonamide sodium salt (9.1 g, 57 mmole) was dissolved in water (40 ml) and acetone (40 ml) was added. To the resulting mixture was added dropwise 40 ml of acetone containing 4-chlorophenyl isocyanate (8.6 g). After two hours solid was removed from the reaction mixture by filtration. The solid was washed with water and the combined filtrate was treated with 1N HCl (57 ml). After about one hour, precipitate was collected from the filtrate and washed with water. After drying at 65° C. under vacuum, 10.7 g of product were obtained.

Workup

  1. customAfter two hours solid was removed from the reaction mixture by filtration
  2. washThe solid was washed with water
  3. additionthe combined filtrate was treated with 1N HCl (57 ml)
  4. customprecipitate was collected from the filtrate
  5. washwashed with water
  6. customAfter drying at 65° C. under vacuum

Sources & evidence

ORD record
ord-e124f0e2b9af4966ad948617031db698
Source dataset
uspto-grants-2000_11
Patent number
US06147115

Reaction notes

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