Tetrahydrofuran → 2-Benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

HRID 1940901Notes

Reaction equation

HRID 1940901 reaction equation
N[C:2]1[C:3]2[N:4]([N:10]=[C:11]([S:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:12]=2)[C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].N(OC(C)(C)C)=O.O1CCCC1>CCOCC>[CH2:14]([S:13][C:11]1[N:12]=[C:3]2[CH:2]=[C:7]([Cl:8])[CH:6]=[C:5]([Cl:9])[N:4]2[N:10]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10906Tert-Butyl nitriteHCID 190807338-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 190807782-Benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8-Amino-2-benzylthio-5,7-dichloro[1,2,4]triazolo[1,5-a]pyridine (25.8 g, 0.079 mol), t-butyl nitrite (18.9 mL, 16.4 g, 0.158 mol) and tetrahydrofuran (1.5 L) were combined and heated at reflux with stirring. Gas evolution began immediately and stopped after a few minutes, but the reaction was heated at reflux for an hour. The volatiles were removed by evaporation under reduced pressure and the residue obtained was chromatographed on silica gel eluting with dichloromethane. The product fractions were concentrated by evaporation under reduced pressure and the residue obtained was mixed with ether. The insoluble solid material was collected by filtration. The ether filtrate was concentrated by evaporation under reduced pressure and the residue was rechromatographed on silica gel eluting with 10 percent ethyl acetate in hexane. The product fractions were concentrated by evaporation under reduced pressure and the residue obtained was combined with the insoluble solid material obtained before to obtain 12.2 g (50 percent of theory) of the title compound as a red-brown powder melting at 88°-89° C.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. waitstopped after a few minutes
  4. temperaturethe reaction was heated
  5. temperatureat reflux for an hour
  6. customThe volatiles were removed by evaporation under reduced pressure
  7. customthe residue obtained
  8. customwas chromatographed on silica gel eluting with dichloromethane
  9. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  10. customthe residue obtained
  11. filtrationThe insoluble solid material was collected by filtration
  12. concentrationThe ether filtrate was concentrated by evaporation under reduced pressure
  13. customthe residue was rechromatographed on silica gel eluting with 10 percent ethyl acetate in hexane
  14. concentrationThe product fractions were concentrated by evaporation under reduced pressure
  15. customthe residue obtained
  16. customobtained before

Sources & evidence

ORD record
ord-305a3074643d482fbc2acc8ff73bc6e6
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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