Pyridinium chloride → HCID 13290059, compound

HRID 485910Notes

Reaction equation

HRID 485910 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 addded 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 2N 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 2N 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-c59474efddce41ecabed82a8137b031e
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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