Acetic Acid → 2-Benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

HRID 1940906Notes

Reaction equation

HRID 1940906 reaction equation
N[C:2]1[C:3]2[N:4]([N:9]=[C:10]([S:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=2)[C:5]([Cl:8])=[CH:6][CH:7]=1.C(O)(=O)C.N(OC(C)(C)C)=O>O1CCCC1>[CH2:13]([S:12][C:10]1[N:11]=[C:3]2[CH:2]=[CH:7][CH:6]=[C:5]([Cl:8])[N:4]2[N:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 190807288-Amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 214644322-Benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8-amino-2-benzylthio-5-chloro[1,2,4]triazolo[1,5-a]pyridine (9.0 g, 0.031 mol) and acetic acid (2.0 g, 0.033 mol) in tetrahydrofuran (100 mL) was added dropwise with stirring over 30 min to a solution of t-butyl nitrite (6.4 g, 0.062 mol) in tetrahydrofuran (500 mL) at 50°-55° C. and allowed to react another 15 minutes after the addition was complete. The volatiles were removed by evaporation under reduced pressure and the residue obtained was chromatographed on silica gel eluting with a gradient of 5-15 percent ethyl acetate in hexane. The product fractions were concentrated by evaporation under reduced pressure to obtain 3.4 g (37 percent of theory) the title compound as a dark low-melting solid.

Workup

  1. customto react another 15 minutes
  2. additionafter the addition
  3. customThe volatiles were removed by evaporation under reduced pressure
  4. customthe residue obtained
  5. customwas chromatographed on silica gel eluting with a gradient of 5-15 percent ethyl acetate in hexane
  6. concentrationThe product fractions were concentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-497d2ec9f3f54953a352fa4ef8ee6c46
Source dataset
uspto-grants-1997_12
Patent number
US05700940

Reaction notes

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