Sodium Hydroxide → HCID 14071527, compound

HRID 1651871Notes

Reaction equation

HRID 1651871 reaction equation
BrBr.[OH-:3].[Na+].C[C:6]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:11]2)=[O:7]>O.O1CCOCC1>[C:21]1([S:18]([NH:17][CH:12]2[CH2:11][C:10]3[C:14](=[CH:15][CH:16]=[C:8]([C:6]([OH:7])=[O:3])[CH:9]=3)[CH2:13]2)(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 14071500N-(5-Acetyl-2,3-dihydro-1H-inden-2-yl)benzenesulfonamide

Product 1

HCID 14071527HCID 14071527, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

12.5 g (0.0795 mol) of bromine are added at -10° C. to a solution of 8.5 g (0.214 mol) of sodium hydroxide in 85 ml of water, and a solution of 5 g (0.015 mol) of 2-benzenesulphonamido-indan-5-yl methyl ketone in 20 ml of dioxan is then added with vigorous stirring. The mixture is stirred for 2 hours at room temperature, the excess bromine is destroyed by adding sodium bisulphite, the alkaline phase is washed with ether and acidified with hydrochloric acid, and the reaction product is extracted with methylene chloride. Evaporation leaves as residue 5.3 g of a resinous substance, which is recrystallised from glacial acetic acid and then from methanol/water.

Workup

  1. customthe excess bromine is destroyed
  2. additionby adding sodium bisulphite
  3. washthe alkaline phase is washed with ether
  4. extractionthe reaction product is extracted with methylene chloride
  5. customEvaporation
  6. customleaves as residue 5.3 g of a resinous substance, which
  7. customis recrystallised from glacial acetic acid

Sources & evidence

ORD record
ord-bfe933945c894818af96008788f8c149
Source dataset
uspto-grants-1990_05
Patent number
US04929754

Reaction notes

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