Carbon Tetrachloride → 8-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

HRID 1940900Notes

Reaction equation

HRID 1940900 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)C=[CH:6][CH:7]=1.[Cl:19]N1C(=O)CCC1=O.[C:27]([Cl:31])(Cl)(Cl)Cl>>[NH2:1][C:2]1[C:3]2[N:4]([N:8]=[C:9]([S:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=2)[C:27]([Cl:31])=[CH:6][C:7]=1[Cl:19]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 31398Chlorosuccinimide2×HCID 190807538-Amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 190807338-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

Procedure

8-Amino-2-benzylthio[1,2,4]triazolo[1,5-a]pyridine (20.0 g, 0.078 mol), N-chlorosuccinimide (10.4 g, 0.078 mol) and carbon tetrachloride were combined and heated to reflux with stirring for 1 hour. The reaction mixture was cooled, more N-chlorosuccinimide (10.4 g) was added, and the reaction heated to reflux with stirring for another hour. The reaction mixture was then cooled and filtered. The filtrate was concentrated by evaporation under reduced pressure and the residue obtained was purified by column chromatography on silica gel eluting with dichloromethane. The product fractions were concentrated by evaporation under reduced pressure and the residues were combined and mixed with ether. The insoluble solids were collected by filtration and dried to obtain 18.0 g (71 percent of theory) of the title compound as a light tan powder melting at 118°-119° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was cooled
  4. temperaturethe reaction heated
  5. temperatureto reflux
  6. stirringwith stirring for another hour
  7. temperatureThe reaction mixture was then cooled
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  10. customthe residue obtained
  11. customwas purified by column chromatography on silica gel eluting with dichloromethane
  12. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  13. additionmixed with ether
  14. filtrationThe insoluble solids were collected by filtration
  15. customdried

Sources & evidence

ORD record
ord-c1a54e887a094e4fbef8e73b02ee9e95
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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