Thionyl Chloride → HCID 57694218, compound

HRID 1678727Notes

Reaction equation

HRID 1678727 reaction equation
[CH2:1]([S:5]([CH:8]1[C:12]([S:13]([CH2:16][CH2:17][CH2:18][CH3:19])(=[O:15])=[O:14])=[CH:11][S:10][CH2:9]1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.P([O-])([O-])(O)=O.[Na+].[Na+].P([O-])(O)(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([S:5]([C:8]1[C:12]([S:13]([CH2:16][CH2:17][CH2:18][CH3:19])(=[O:14])=[O:15])=[CH:11][S:10][CH:9]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 67333945HCID 67333945, compound2×HCID 86630341Sodium phosphate (Na3(PO4)2)

Product 1

HCID 57694218HCID 57694218, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Under a nitrogen atmosphere, 3,4-bis(butane-1-sulfonyl)dihydrothiophene and chloroform were placed in a reaction vessel to dissolve 3,4-bis(butane-1-sulfonyl)-dihydrothiophene in chloroform. To the solution, thionyl chloride (3.0 equivalents) was added, followed by heating under reflux for 36 hours. A disodium hydrogenphosphate/sodium dihydrogenphosphate buffer which had been adjusted to pH 7 was added to the reaction mixture to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The organic layer was washed three times with saturated brine, and was dried over anhydrous sodium sulfate. The solvent was distilled off. The resultant crude product was purified through a silica gel column (hexane:ethyl acetate=2:1) to obtain the reaction product.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 36 hours
  3. additionwas added to the reaction mixture
  4. customto quench
  5. customthe reaction
  6. extractionthe reaction mixture was extracted with ethyl acetate
  7. washThe organic layer was washed three times with saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customThe resultant crude product was purified through a silica gel column (hexane:ethyl acetate=2:1)
  11. customto obtain the reaction product

Sources & evidence

ORD record
ord-45465ef09fe3476fb5a70a91ed727458
Source dataset
uspto-grants-2011_08
Patent number
US08008425B2

Reaction notes

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