Phosphorus pentachloride → Ethyl 3-(chlorosulfonyl)propanoate

HRID 1906386Notes

Reaction equation

HRID 1906386 reaction equation
[C:1]([CH2:6][CH2:7][S:8]([O-:11])(=O)=[O:9])([O:3][CH2:4][CH3:5])=[O:2].[Na+].P(Cl)(Cl)(Cl)(Cl)[Cl:14]>C(Cl)(Cl)Cl>[C:1]([CH2:6][CH2:7][S:8]([Cl:14])(=[O:11])=[O:9])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23688422Sodium 2-carboethoxyethyl sulfonate

Product 1

HCID 4128467Ethyl 3-(chlorosulfonyl)propanoateYield 32.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 90.5 g (0.44 moles) sodium 2-carboethoxyethyl sulfonate (the product of Example 26) in 300 ml chloroform, 92 g (0.44 moles) phosphorus pentachloride was added in small portions, maintaining the temperature of the reaction mixture below 40° C. during the addition. The reaction mixture was refluxed for about 6 hours, and then filtered. Nitrogen was bubbled through the solution to remove excess hydrogen chloride gas. Stripping of the solvent gave 28.4 g of the above-identified product.

Workup

  1. temperaturemaintaining the temperature of the reaction mixture below 40° C.
  2. additionduring the addition
  3. temperatureThe reaction mixture was refluxed for about 6 hours
  4. filtrationfiltered
  5. customNitrogen was bubbled through the solution
  6. customto remove excess hydrogen chloride gas

Sources & evidence

ORD record
ord-c014c098d5a945b49ccac70f88bc95ba
Source dataset
uspto-grants-1987_03
Patent number
US04652556

Reaction notes

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