Pyridinium chloride → HCID 13290059, compound

HRID 1903501Notes

Reaction equation

HRID 1903501 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[Cl: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[Cl:16])[S:7][C:6]=2[C:17]=1[Cl:18]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290058HCID 13290058, compound

Product 1

HCID 13290059HCID 13290059, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 26.8 g of 6,7-dichloro-2-(2'-chlorophenyl)-5-methoxybenzo[b]thiophene and 260 g of pyridine hydrochloride is heated at 190°-200° for 4.5 hrs. To the cooled mixture is added 800 ml of water and the aqueous mixture is extracted with three 400-ml portions of ethyl ether. The organic layers are collected, washed with 400 ml of 2 N hydrochloric acid and with 200 ml of water. The organic layer is dried over anhydrous magnesium sulfate, decolorized (charcoal) overnight and the solvent is removed. Recrystallization from acetone-hexane gives 18.6 g of 6,7-dichloro-2-(2'-chlorophenyl)-5-hydroxybenzo[b]thiophene, mp 174°-175°.

Workup

  1. temperatureis heated at 190°-200° for 4.5 hrs
  2. extractionthe aqueous mixture is extracted with three 400-ml portions of ethyl ether
  3. customThe organic layers are collected
  4. washwashed with 400 ml of 2 N hydrochloric acid and with 200 ml of water
  5. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  6. custom(charcoal) overnight
  7. customthe solvent is removed
  8. customRecrystallization from acetone-hexane

Sources & evidence

ORD record
ord-047880c04d6449598fdadba9b8d76a84
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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