Water → HCID 19360258, compound

HRID 376873Notes

Reaction equation

HRID 376873 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.Cl.[Cl:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[ClH:12].[N:16]1[CH:17]=[CH:18][C:13]([NH:1][C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochlorideHCID 111944231-Benzothiophen-3-amine

Product 1

HCID 19360258HCID 19360258, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-aminobenzo[b]thiophene (3 g, 20 mmol) and 4-chloropyridine hydrochloride (3.5 g, 23 mmol) in 50 mL of 1-methyl-2-pyrrolidinone was stirred at 80° for three hours, and thereafter cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride solution and dried (anhydrous magnesium sulfate), filtered and concentrated to 8 g dark oil. Elution through silica with ethyl acetate via flash column chromatography yielded 5 g of an amber oil. Conversion to the hydrochloride salt in methanol-ether yielded 3 g of a hygroscopic solid. Recrystallization from 50% methanol in ether yielded 1.8 g of rust colored crystals, mp 268-270° (dec.).

Workup

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

Sources & evidence

ORD record
ord-d864e4a886cd48c6a5cc12dc20a36fc8
Source dataset
uspto-grants-2000_02
Patent number
US06022880

Reaction notes

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