Pyridinium chloride → HCID 13290020, compound

HRID 370956Notes

Reaction equation

HRID 370956 reaction equation
[Cl:1][C:2]1[C:3]([O:15]C)=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[S:7][C:6]=2[C:13]=1[Cl:14].Cl.N1C=CC=CC=1>>[Cl:1][C:2]1[C:3]([OH:15])=[CH:4][C:5]2[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[S:7][C:6]=2[C:13]=1[Cl:14]

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 13290019HCID 13290019, compound

Product 1

HCID 13290020HCID 13290020, compoundYield 98.5%

Procedure

A mixture of 6.00 g of 6,7-dichloro-2-isopropyl-5-methoxybenzo[b]thiophene and 50 g of pyridine hydrochloride, is heated under nitrogen with stirring in a 185° bath for 4.5 hours and at 200° for one hour. The reaction is cooled, triturated with 500 ml of water and extracted with three 150 ml-portions of ether. The combined ether extracts are washed with one 150 ml-portion of 2N hydrochloric acid, two 150 ml-portions of water and one 50 ml-portion of saturated sodium chloride solution and dried over magnesium sulfate to give 5.61 g of 6,7-dichloro-5-hydroxy-2-isopropylbenzo[b]thiophene as an amber oil which crystallized on standing to a product having mp 44.5-46.5. A sample recrystallized twice from hexane melts at 44.5°-46.5°.

Workup

  1. temperatureis heated under nitrogen
  2. waitat 200° for one hour
  3. temperatureThe reaction is cooled
  4. customtriturated with 500 ml of water
  5. extractionextracted with three 150 ml-portions of ether
  6. washThe combined ether extracts are washed with one 150 ml-portion of 2N hydrochloric acid, two 150 ml-portions of water and one 50 ml-portion of saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-bda3e42c1fb44ed3b2577755e57837aa
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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