Sodium hydrosulfide → 2-Chloro-4-(ethylsulfonyl)benzenethiol

HRID 910833Notes

Reaction equation

HRID 910833 reaction equation
[SH-:1].[Na+].[CH2:3]([S:5]([C:8]1[CH:13]=[CH:12][C:11](F)=[C:10]([Cl:15])[CH:9]=1)(=[O:7])=[O:6])[CH3:4]>CN(C=O)C.[OH-].[Na+]>[Cl:15][C:10]1[CH:9]=[C:8]([S:5]([CH2:3][CH3:4])(=[O:7])=[O:6])[CH:13]=[CH:12][C:11]=1[SH:1]

Participants

5

Reactant 2

HCID 28015Sodium hydrosulfideHCID 579047252-Chloro-4-(ethylsulfonyl)-1-fluorobenzene

Product 1

HCID 673906392-Chloro-4-(ethylsulfonyl)benzenethiol

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

Sodium hydrosulphide (0.252 g) was added to the product from example 4 step (i) (11.0 g) in dry DMF (10 ml) and stirred at RT for 2 h. The mixture was diluted with 2M sodium hydroxide solution and extracted with diethylether. The aqueous layer was acidified with 2M hydrochloric acid, extracted with ethyl acetate, dried and evaporated under reduced pressure, crude yield 1.60 g.

Workup

  1. extractionextracted with diethylether
  2. extractionextracted with ethyl acetate
  3. customdried
  4. customevaporated under reduced pressure, crude yield 1.60 g

Sources & evidence

ORD record
ord-2c5ad7ee73c7461dbae0cf95dc3459cd
Source dataset
uspto-grants-2011_09
Patent number
US08022248B2

Reaction notes

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