Pyridinium chloride → HCID 13290077, compound

HRID 1903514Notes

Reaction equation

HRID 1903514 reaction equation
[Cl:1][C:2]1[C:3]([O:16]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290076HCID 13290076, compound

Product 1

HCID 13290077HCID 13290077, compoundYield 70.1%

Procedure

A mixture of 12 g of 6,7-dichloro-5-methoxy-2-isobutylbenzo[b]thiophene and 130 g of pyridine hydrochloride is heated at 190°-200° for 4 hrs. The cooled mixture is poured onto ice and extracted with ether. The ether extracts are washed with 10% hydrochloric acid, water, dried over anhydrous magnesium sulfate-charcoal and filtered. Evaporation of the filtrate affords an oil. Chromatography of the oil on silica gel gives 8.0 g of 6,7-dichloro-5-hydroxy-2-isobutylbenzo[b]thiophene, mp 58°-59°.

Workup

  1. temperatureis heated at 190°-200° for 4 hrs
  2. additionThe cooled mixture is poured onto ice
  3. extractionextracted with ether
  4. washThe ether extracts are washed with 10% hydrochloric acid, water
  5. dry with materialdried over anhydrous magnesium sulfate-charcoal
  6. filtrationfiltered
  7. customEvaporation of the filtrate
  8. customaffords an oil

Sources & evidence

ORD record
ord-25e948a2406d44f695e42c952ba9da53
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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