Pyridinium chloride → HCID 13290051, compound

HRID 652673Notes

Reaction equation

HRID 652673 reaction equation
[Cl:1][C:2]1[C:3]([O:18]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[S:7][C:6]=2[C:16]=1[Cl:17].Cl.N1C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)[S:7][C:6]=2[C:16]=1[Cl:17]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290035HCID 13290035, compound

Product 1

HCID 13290051HCID 13290051, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.0 of 6,7-dichloro-2-cyclohexyl-5-methoxybenzo[b]thiophene and 50 g of pyridine hydrochloride is stirred at 195° for 5 hrs. The cooled mixture is diluted with 250 ml of water and the resulting aqueous mixture is extracted with 3×250 ml ether. The organic layers are combined, washed with 150 ml of 2N hydrochloric acid, 2×100 ml of water, dried over anhydrous magnesium sulfate and filtered. The solvent is removed and the residue is chromatographed on a silical gel column using hexane and then 1:1 ether-hexane as eluting solvents. Evaporation of the eluents gives 3.2 g of 6,7-dichloro-2-cyclohexyl-5-hydroxybenzo[b]thiophene. Crystallization from pentane gives the analytical sample, mp 59°-60°.

Workup

  1. extractionthe resulting aqueous mixture is extracted with 3×250 ml ether
  2. washwashed with 150 ml of 2N hydrochloric acid, 2×100 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent is removed
  6. customthe residue is chromatographed on a silical gel column
  7. wash1:1 ether-hexane as eluting solvents
  8. customEvaporation of the eluents

Sources & evidence

ORD record
ord-5f2902ef30f44e31be7bd253ba4618f0
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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