Pyridinium chloride → HCID 20197874, compound

HRID 485885Notes

Reaction equation

HRID 485885 reaction equation
[Cl:1][C:2]1[C:3]([O:19]C)=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[S:7][C:6]=2[C:17]=1[Cl:18].Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([OH:19])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[F:16])[S:7][C:6]=2[C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290031HCID 13290031, compound

Product 1

HCID 20197874HCID 20197874, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.0 g of 6,7-dichloro-5-methoxy-2-(2'-fluorophenyl)benzo[b]thiophene and 150 g of pyridine hydrochloride is heated at 200°-250° for 1 hour with stirring under an atmosphere of nitrogen. The mixture is allowed to cool, diluted with water and the precipitate is collected. The precipitate is dissolved in dichloromethane and the solution is washed with water, dried and filtered. Evaporation of the solvent followed by treatment of the mixture with ether-hexane gives 13.2 g of 6,7-dichloro-2-(2'-fluorophenyl)-5-hydroxybenzo[b]thiophene as an amorphous solid.

Workup

  1. temperatureis heated at 200°-250° for 1 hour
  2. temperatureto cool
  3. customthe precipitate is collected
  4. dissolutionThe precipitate is dissolved in dichloromethane
  5. washthe solution is washed with water
  6. customdried
  7. filtrationfiltered
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-2ef658727299488d8e7cabe5f61e00e7
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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