Pyridinium chloride → HCID 13290016, compound

HRID 370950Notes

Reaction equation

HRID 370950 reaction equation
[Cl:1][C:2]1[C:3]([O:19]C)=[CH:4][C:5]2[C:9]([CH3:10])=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:7][C:6]=2[C:17]=1[Cl:18].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:19])=[CH:4][C:5]2[C:9]([CH3:10])=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:7][C:6]=2[C:17]=1[Cl:18]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290015HCID 13290015, compound

Product 1

HCID 13290016HCID 13290016, compoundYield 75.3%

Procedure

A mixture of 2.5 g of 6,7-dichloro-5-methoxy-3-methyl-2-phenyl benzo[b]thiophene and 20 g of pyridine hydrochloride is stirred at 185°-190° for 3 hours. The cooled mixture is triturated with water and extracted 3 times with ether. The combined ether extracts is washed with dilute hydrochloric acid, water and dried. Removal of solvent leaves a brownish solid which is purified by passing it through a silica gel column packed in hexane. Elution with 50:50 ether-hexane gave 1.8 g of 6,7-dichloro-5-hydroxy-3-methyl-2-phenylbenzo[b]thiophene as colorless crystals, mp 146°-147°. For analysis, a sample is recrystallized twice from ether-hexane (10% of ether) and dried at 100°.

Workup

  1. customThe cooled mixture is triturated with water
  2. extractionextracted 3 times with ether
  3. washThe combined ether extracts is washed with dilute hydrochloric acid, water
  4. customdried
  5. customRemoval of solvent
  6. customleaves a brownish solid which
  7. customis purified
  8. washElution with 50:50 ether-hexane

Sources & evidence

ORD record
ord-46c75e7518f849b3a7611c5c3a014be5
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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