Acetonitrile → 2-Benzylthio-5,8-dichloro[1,2,4]triazolo[1,5-a]pyridine

HRID 1940909Notes

Reaction equation

HRID 1940909 reaction equation
C(#N)C.N(OC(C)(C)C)=O.N[C:12]1[C:13]2[N:14]([N:19]=[C:20]([S:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:21]=2)[C:15]([Cl:18])=[CH:16][CH:17]=1.[Cl:30]CCl>Cl.[Cu]Cl>[CH2:23]([S:22][C:20]1[N:21]=[C:13]2[C:12]([Cl:30])=[CH:17][CH:16]=[C:15]([Cl:18])[N:14]2[N:19]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 10906Tert-Butyl nitriteHCID 190807288-Amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 190807452-Benzylthio-5,8-dichloro[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 9.9 g (0.10 mol) of copper(I) chloride with 300 mL of acetonitrile was prepared and 8.7 mL (6.8 g, 0.066 mol) of 90 percent t-butyl nitrite was added with stirring. After 10 minutes 9.5 g (0.033 mol) of 8-amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine was added and the reaction mixture was allowed to react with stirring for 3 days. The mixture was then diluted with dichloromethane and 2N aqueous hydrochloric acid, and after mixing this well, the phases were separated. The organic layer was washed with 2N aqueous hydrochloric acid and concentrated by evaporation under reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane to obtain 6.5 g (63 percent of theory) of the title compound as a yellow powder melting at 103°-104° C.

Workup

  1. customwas prepared
  2. customto react
  3. stirringwith stirring for 3 days
  4. additionafter mixing this well, the phases
  5. customwere separated
  6. washThe organic layer was washed with 2N aqueous hydrochloric acid
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customThe residue was chromatographed on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-f83f63456fc54741b63400dab5554fd7
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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