Water → HCID 19360267, compound

HRID 376878Notes

Reaction equation

HRID 376878 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:4]=2[S:5][CH:6]=1.Cl.Cl[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.O>CN1CCCC1=O>[ClH:11].[Cl:11][C:8]1[CH:9]=[CH:10][C:3]2[C:2]([NH:1][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:6][S:5][C:4]=2[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 818524-Chloropyridine hydrochlorideHCID 193602466-Chlorobenzo[b]thiophen-3-amine

Product 1

HCID 19360267HCID 19360267, compoundYield 174.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-amino-6-chlorobenzo[b]thiophene (5 g, 27 mmol) and 4-chloropyridine hydrochloride (6 g, 40 mmol) in 75 mL of 1-methyl-2-pyrrolidinone was stirred at 80° for 1.5 h, and then was cooled, stirred with water and extracted with ether. The aqueous layer was basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution and then was dried (anhydrous magnesium sulfate), filtered and concentrated to a dark oil. Elution through silica with ethyl acetate via flash column chromatography yielded 7 g of an amber oil. Conversion to the hydrochloride salt in 20% methanol in ether yielded 4.2 g of yellow crystals, mp 264-266° (dec.).

Workup

  1. temperaturewas cooled
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialwas dried (anhydrous magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated to a dark oil
  9. washElution through silica with ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-ff2904357f9044cdb9e736b5536b9fe2
Source dataset
uspto-grants-2000_02
Patent number
US06022880

Reaction notes

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