Pyridinium chloride → HCID 13290055, compound

HRID 370998Notes

Reaction equation

HRID 370998 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[CH3:16])[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[CH3:16])[S:7][C:6]=2[C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290054HCID 13290054, compound

Product 1

HCID 13290055HCID 13290055, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4.0 g of 6,7-dichloro-5-methoxy-2-(2'-methylphenyl)benzo[b]thiophene and 40 g of pyridine hydrochloride is heated at 200°-205° for 3 hrs. To the cooled mixture is added 250 ml of water and the aqueous mixture is extracted with three 200 ml-portions of ethyl ether. The organic layers are combined, washed dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization of the residue from ether-pentane gives 2.8 g of 6,7-dichloro-5-hydroxy-2-(2'-methylphenyl)benzo[b]thiophene, mp 106°-107°.

Workup

  1. temperatureis heated at 200°-205° for 3 hrs
  2. extractionthe aqueous mixture is extracted with three 200 ml-portions of ethyl ether
  3. washwashed
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. customRecrystallization of the residue from ether-pentane

Sources & evidence

ORD record
ord-19eb03e50d3947f084e8aa861475cdcd
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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