Pyridine → HCID 20341558, compound

HRID 971823Notes

Reaction equation

HRID 971823 reaction equation
O[CH2:2][CH2:3][S:4]([CH:7]([CH:14]=[CH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])=[O:5].N1C=CC=CC=1.S(Cl)([Cl:24])=O>O1CCCC1.[N+](C1C=CC=C([N+]([O-])=O)C=1)([O-])=O>[Cl:24][CH2:2][CH2:3][S:4]([CH:7]([CH:14]=[CH2:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])=[O:5]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20341559HCID 20341559, compound

Product 1

HCID 20341558HCID 20341558, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 74521,3-DinitrobenzeneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 50 g (0.221 moles) of vinylbenzyl 2-hydroxyethyl sulfone, 19.2 g (0.243 moles) of pyridine, and 1 g of m-dinitrobenzene in 500 ml of tetrahydrofuran at 0° to 5° C. was added dropwise 28.9 g (0.243 moles) of thionyl chloride. After the addition was complete, the mixture was refluxed for 2 hours, cooled to 0° to 5° C., and the pyridine hydrochloride was removed by filtration. The solvent was then evaporated to leave an oil which was added to one liter of ice water to crystallize the product. The solid was collected by filtration and recrystallized from 1.6 liters of 50 percent water, 50 percent ethanol to give 46 g (85.2 percent) of the desired product (mp 62° to 84° C.).

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was refluxed for 2 hours
  3. temperaturecooled to 0° to 5° C.
  4. customthe pyridine hydrochloride was removed by filtration
  5. customThe solvent was then evaporated
  6. customto leave an oil which
  7. customto crystallize the product
  8. filtrationThe solid was collected by filtration
  9. customrecrystallized from 1.6 liters of 50 percent water, 50 percent ethanol

Sources & evidence

ORD record
ord-261fd65744f14fbe8f959d87a74b3a9a
Source dataset
uspto-grants-1979_07
Patent number
US04161407

Reaction notes

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