Sodium Carbonate → HCID 15342496, compound

HRID 440311Notes

Reaction equation

HRID 440311 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 (anhydrous 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 (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. washGradient elution through silica with dichloromethane

Sources & evidence

ORD record
ord-ca649a68ecd54cd4ae35a010c9668bea
Source dataset
uspto-grants-1996_05
Patent number
US05519032

Reaction notes

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