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

HRID 1586842Notes

Reaction equation

HRID 1586842 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-9bd9920965864ceab183c25461b6be0a
Source dataset
uspto-grants-1993_06
Patent number
US05216026

Reaction notes

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