Pyridinium chloride → HCID 13290070, compound

HRID 371006Notes

Reaction equation

HRID 371006 reaction equation
[Cl:1][C:2]1[C:3]([O:15]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[S:7][C:6]=2[C:13]=1[Cl:14].Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([OH:15])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][CH3:12])[S:7][C:6]=2[C:13]=1[Cl:14]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 139528716,7-Dichloro-5-methoxy-2-n-propylbenzo[b]thiophene

Product 1

HCID 13290070HCID 13290070, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 29 g of 6,7-dichoro-5-methoxy-2-n-propylbenzo[b]thiophene and 280 g of pyridine hydrochloride is heated at 190° for 5 hrs and allowed to cool. The reaction mixture is poured into 300 ml of water and extracted with three 33-ml portions of ether. The ether extracts are washed with 500 ml of 2N hydrochloric acid, water, dried over anhydrous magnesium sulfate-charcoal, filtered and evaporated to give an oil. Crystallization of the oil with hexane followed by recrystallization from hexane give 15.5 g of 6,7-dichloro-5-hydroxy-2-n-propylbenzo[b]thiophene, mp 50°-51°.

Workup

  1. temperatureis heated at 190° for 5 hrs
  2. temperatureto cool
  3. extractionextracted with three 33-ml portions of ether
  4. washThe ether extracts are washed with 500 ml of 2N hydrochloric acid, water
  5. dry with materialdried over anhydrous magnesium sulfate-charcoal
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. customCrystallization of the oil with hexane
  10. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-169cbc9ce568434b99780b4e412998bb
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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