Sodium Carbonate → HCID 15342496, compound

HRID 341820Notes

Reaction equation

HRID 341820 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.Cl.Cl[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[N:16]1[CH:17]=[CH:18][C:13]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][N:7]=[CH:8][CH:9]=3)[S:4][CH:3]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 818524-Chloropyridine hydrochlorideHCID 15342498Thieno[2,3-c]pyridin-3-amine

Product 1

HCID 15342496HCID 15342496, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 3-aminothieno[2,3-c]pyridine (10 g) and 4-chloropyridine hydrochloride (10 g) in 200 mL of 1-methyl-2-pyrrolidinone was stirred at 80° C. for four hours, and then was cooled, stirred with ice-water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed with water and saturated sodium chloride, and then was dried (an hydrous magnesium sulfate), filtered and evaporated. Gradient elution through silica with dichloromethane followed by 10% methanol in dichloromethane afforded 4 g (26%) of a tan solid, m.p. 236°-238° C.

Workup

  1. temperaturewas cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and saturated sodium chloride
  5. dry with materialwas dried (an hydrous magnesium sulfate),
  6. filtrationfiltered
  7. customevaporated
  8. washGradient elution through silica with dichloromethane

Sources & evidence

ORD record
ord-09e35ee5e1054523a3bab8f59376d857
Source dataset
uspto-grants-1999_01
Patent number
US05856335

Reaction notes

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