Water → Sulofenur

HRID 651494Notes

Reaction equation

HRID 651494 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 1 N 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 1 N 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 1 N 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-72b834efd24b4476afd29a79238290db
Source dataset
uspto-grants-2001_08
Patent number
US06281240B1

Reaction notes

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