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

HRID 1898814Notes

Reaction equation

HRID 1898814 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, i0.062 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) of 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-8944d8903e25480da14c59913a0eda28
Source dataset
uspto-grants-1996_11
Patent number
US05571775

Reaction notes

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