Hydrochloric Acid → 4-(Phenylsulfonyl)benzenethiol

HRID 2372812

Reaction equation

HRID 2372812 reaction equation
C[S-:2].[Na+].Cl[C:5]1[CH:10]=[CH:9][C:8]([S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.Cl>CN(C)P(N(C)C)(N(C)C)=O>[C:14]1([S:11]([C:8]2[CH:7]=[CH:6][C:5]([SH:2])=[CH:10][CH:9]=2)(=[O:13])=[O:12])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6621SulphenoneHCID 4378561Sodium methanethiolate

Product 1

HCID 129632484-(Phenylsulfonyl)benzenethiolYield 301%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
100 °C

Procedure

1.25 g of sodium thiomethylate are added under a nitrogen atmosphere to a solution of 15 g (0.0593 mol) of 1-chloro-4-(phenylsulfonyl)benzene in 150 ml of hexamethylphosphoramide. The mixture obtained is heated for 4 hours at 100° C. and then cooled and hydrolyzed in an ice/water mixture. The reaction medium obtained is extracted with ethyl acetate and the aqueous phase obtained is then poured into a 4 N solution of hydrochloric acid at 0° C. The product formed precipitates. After filtration, washing with water until the pH of the washings is neutral, and drying, 13.44 g (yield: 90.5%) of the expected product are obtained. M.p.=117° C.

Workup

  1. customThe mixture obtained
  2. temperaturecooled
  3. customThe reaction medium obtained
  4. extractionis extracted with ethyl acetate
  5. customthe aqueous phase obtained
  6. customThe product formed
  7. customprecipitates
  8. filtrationAfter filtration
  9. washwashing with water until the pH of the washings
  10. customdrying

Sources & evidence

ORD record
ord-45a9defbeff149f0824b9d6bf7687f3f
Source dataset
uspto-grants-1992_03
Patent number
US05100913

Linked notes

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