Pyridinium chloride → HCID 13290048, compound

HRID 1903495Notes

Reaction equation

HRID 1903495 reaction equation
[Cl:1][C:2]1[C:3]([O:16]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][CH3:13])[S:7][C:6]=2[C:14]=1[Cl:15].Cl.N1C=CC=CC=1>O>[CH2:10]([C:8]1[S:7][C:6]2[C:14]([Cl:15])=[C:2]([Cl:1])[C:3]([OH:16])=[CH:4][C:5]=2[CH:9]=1)[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13952872HCID 13952872, compound

Product 1

HCID 13290048HCID 13290048, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 g of 6,7-dichloro-2-n-butyl-5-methoxybenzo[b]thiophene and 50 g of pyridine hydrochloride, under nitrogen, is heated with stirring in a 195° oil-bath for 5 hrs. After the reaction mixture has cooled, 1000 ml of water is added and the aqueous mixture is extracted with three 250-ml portions of ether. The organic layers are combined, washed with one 200-ml portion of 2 N hydrochloric acid, two 250-ml portions of water, dried over anhydrous magnesium sulfate and filtered. The solvent is removed to give an oil. Crystallization with pentane and cooling gives 3.3 g of 2-n-butyl-6,7-dichloro-5-hydroxybenzo[b]thiophene, mp 35°.

Workup

  1. temperatureunder nitrogen, is heated
  2. temperatureAfter the reaction mixture has cooled
  3. extractionthe aqueous mixture is extracted with three 250-ml portions of ether
  4. washwashed with one 200-ml portion of 2 N hydrochloric acid, two 250-ml portions of water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed
  8. customto give an oil
  9. customCrystallization with pentane
  10. temperaturecooling

Sources & evidence

ORD record
ord-b66de9157a5e4b4ab8a9902733ecf7b2
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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