Pyridine → HCID 68726642, compound

HRID 660049Notes

Reaction equation

HRID 660049 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][CH2:17]O)(=[O:15])=[O:14])=[CH:9][CH:8]=1)[CH3:6].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][CH2:17][CH2:16][S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:5][CH3:6])=[CH:8][CH:9]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 2758891HCID 2758891, compound

Product 1

HCID 68726642HCID 68726642, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.0 ml (14.0 mmol) of thionyl chloride in toluene (15 ml) was added dropwise, while cooling with ice, to a solution of 1.0 g (4.67 mmol) of 2-(4-ethylphenylsulfonyl)-ethanol and 56 μl (0.70 mmol) of pyridine in toluene (20 ml). The mixture was then heated for 3 h under reflux. Quenching with ice and water was then carried out. The phases were separated and the aqueous phase was extracted twice with DCM. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. There were obtained as crude product 1.19 g of slightly impure 1-(2-chloroethylsulfonyl)-4-ethylbenzene, which was reacted further without additional purification.

Workup

  1. temperatureThe mixture was then heated for 3 h
  2. temperatureunder reflux
  3. customQuenching with ice and water
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted twice with DCM
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41a18342f66842349cdf839c596a1080
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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