Pyridinium chloride → HCID 13290001, compound

HRID 370945Notes

Reaction equation

HRID 370945 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 1N 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 1N 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-c627ea9b3b394d03b576a4ede41276b6
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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