Pyridinium chloride → HCID 13290010, compound

HRID 485851Notes

Reaction equation

HRID 485851 reaction equation
[Cl:1][C:2]1[C:3]([O:14]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290009HCID 13290009, compound

Product 1

HCID 13290010HCID 13290010, compoundYield 73.7%

Procedure

A mixture of 2.15 g of 6,7-dichloro-2-ethyl-5-methoxybenzo[b]thiophene and 15 g of pyridine hydrochloride is stirred at 170°-180° for 90 min. The mixture is cooled, triturated with water and extracted three times with dichloromethane. The combined organic extracts are washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to an oily residue. Purification by column chromatography (silica gel-ether-pentane 50:50) affords 1.5 g of 6,7-dichloro-2-ethyl-5-hydroxybenzo[b]thiophene as off-white crystals, mp 69°-70°.

Workup

  1. temperatureThe mixture is cooled
  2. customtriturated with water
  3. extractionextracted three times with dichloromethane
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo to an oily residue
  7. customPurification by column chromatography (silica gel-ether-pentane 50:50)

Sources & evidence

ORD record
ord-a1d42776a35648b9b5e5f3949da22022
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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