Sodium Hydroxide → N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamide

HRID 354556Notes

Reaction equation

HRID 354556 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][C:11]2=[O:14])=[CH:7][C:6]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17].[OH-].[Na+].[BH4-].[Na+]>CO>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:13]=[C:12]2[C:8]([CH2:9][CH2:10][CH:11]2[OH:14])=[CH:7][C:6]=1[NH:15][S:16]([CH3:19])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 71246FlosulideHCID 4311764Sodium borohydride

Product 1

HCID 13084202N-[6-(2,4-difluorophenoxy)1-hydroxy-5-indanyl]methanesulfonamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.53 g of 6-(2,4-difluorophenoxy)-5-methylsulfonylamino-1-indanone was dissolved in 35 ml of methanol and 10 ml of 1 N sodium hydroxide solution and, at 5° C., combined in incremental portions with 0.8 g of sodium borohydride. After 16 hours at 20° C., the mixture was concentrated, mixed with 40 ml of water and 26 ml of 1 N hydrochloric acid, and vacuum-filtered. Recrystallization from ethanol yielded 3.07 g of N-[6-(2,4-difluorophenoxy)-1-hydroxy-5-indanyl]methanesulfonamide, mp 127° C.

Workup

  1. customat 5° C.
  2. concentrationthe mixture was concentrated
  3. additionmixed with 40 ml of water and 26 ml of 1 N hydrochloric acid
  4. filtrationvacuum-filtered
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-961bdfbe415448548b2375cee181a0fd
Source dataset
uspto-grants-1983_03
Patent number
US04375479

Reaction notes

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