Pyridinium chloride → HCID 13290001, compound

HRID 1903445Notes

Reaction equation

HRID 1903445 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[C:15]([O:17]C)[C:14]([Cl:19])=[C:13]([Cl:20])[C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1>O>[Cl:19][C:14]1[C:15]([OH:17])=[CH:16][C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:12][S:11][C:10]=2[C:13]=1[Cl:20]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13289998HCID 13289998, compound

Product 1

HCID 13290001HCID 13290001, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 200 mg of 3-(4-chlorophenyl)-6,7-dichloro-5-methoxybenzo[b]thiophene and 1.77 g of pyridine hydrochloride is stirred and heated at 195°-205° for two and one half hours. The reaction is cooled and 20 ml of water is added. The resulting solid is collected on a filter and washed with 1 N hydrochloric acid. The product is chromatographed on a silica gel-hexane column using 3:1 hexane/ether as elutent. The product is isolated and recrystallized from acetone-hexane to give 150 mg of 6,7-dichloro-3-(4-chlorophenyl)-5-hydroxybenzo[b]thiophene as a white powder, mp 174°-176°.

Workup

  1. temperatureheated at 195°-205° for two and one half hours
  2. temperatureThe reaction is cooled
  3. customThe resulting solid is collected on
  4. filtrationa filter
  5. washwashed with 1 N hydrochloric acid
  6. customThe product is chromatographed on a silica gel-hexane column
  7. customThe product is isolated
  8. customrecrystallized from acetone-hexane

Sources & evidence

ORD record
ord-ff5f73f0236e47aba9dae2860c2e666e
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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