Phosphorus pentachloride → 1-Benzothiophene-3-sulfonyl chloride

HRID 392033

Reaction equation

HRID 392033 reaction equation
[Na].[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([S:11]([O-:14])(=O)=[O:12])=[CH:3]1.P(Cl)(Cl)(Cl)(Cl)[Cl:16]>P(Cl)(Cl)(Cl)=O>[Cl:16][S:11]([C:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:2][CH:3]=1)(=[O:14])=[O:12]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 86584280HCID 86584280, compound

Product 1

HCID 27763401-Benzothiophene-3-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent2×

Procedure

180 g of sodium-benzothiophene-3-sulphonate are placed in 650 ml of phosphorus oxychloride and then combined with 156 g of phosphorus pentachloride. The reaction mixture is refluxed for 3.5 hours before the excess phosphorus oxychloride is eliminated by distillation in vacuo. The residue is taken up in 800 ml of chloroform and the precipitate formed is separated off by filtering. The filtrate is concentrated by evaporation and stirred into 800 ml of petroleum ether with heating. The crystalline substance thus precipitated is filtered off, washed with petroleum ether and dried at 35° C. Yield: 113 g. M.p.: 88-89° C.

Workup

  1. distillationis eliminated by distillation in vacuo
  2. customthe precipitate formed
  3. customis separated off
  4. filtrationby filtering
  5. concentrationThe filtrate is concentrated by evaporation
  6. temperaturewith heating
  7. customThe crystalline substance thus precipitated
  8. filtrationis filtered off
  9. washwashed with petroleum ether
  10. customdried at 35° C

Sources & evidence

ORD record
ord-2f313a02e95a42bdab0d32630808a91f
Source dataset
uspto-grants-2004_10
Patent number
US06800623B2

Linked notes

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