Water → Sulofenur

HRID 233810Notes

Reaction equation

HRID 233810 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.O>CC(C)=O>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:13][S:10]([C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[CH2:1][CH2:2][CH2:3]3)(=[O:11])=[O:12])=[O:25])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 96876Indan-5-sulphonamide

Product 1

HCID 60417SulofenurYield 87.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 93.2 g of 2,3-dihydro-5-indenylsulfonamide in 300 ml of acetone were added 490 ml of a 1N sodium hydroxide solution. A solution of 79.36 g of 4-chlorophenylisocyanate in 250 ml of acetone was added to the reaction mixture with stirring. After stirring at room temperature for 18 hours, the reaction mixture was filtered and 490 ml of 1N hydrochloric acid were added to the filtrate thereby providing a fine white precipitate. One liter of water was added, and the solid was recovered by filtration to provide 144.86 g of the desired title product, m.p. 169°-172° C.

Workup

  1. stirringAfter stirring at room temperature for 18 hours
  2. filtrationthe reaction mixture was filtered
  3. addition490 ml of 1N hydrochloric acid were added to the filtrate
  4. customthereby providing a fine white precipitate
  5. filtrationthe solid was recovered by filtration

Sources & evidence

ORD record
ord-704b5dc943ae48e88f6176ffeadc3973
Source dataset
uspto-grants-1997_01
Patent number
US05594028

Reaction notes

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