Water → Sulofenur

HRID 326692Notes

Reaction equation

HRID 326692 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 mixture of 93.2 g of indane-5-sulfonamide in 300 ml of acetone were added 490 ml of 1N sodium hydroxide. 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 about 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 about 18 hours
  2. filtrationthe reaction mixture was filtered
  3. addition490 ml of 1N hydrochloric acid were added to the filtrate
  4. customproviding a fine white precipitate
  5. filtrationthe solid was recovered by filtration

Sources & evidence

ORD record
ord-b6903433080c4d53a6c1818eaaef482f
Source dataset
uspto-grants-1993_12
Patent number
US05270329

Reaction notes

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