Diethyl Ether → 6-Bromo-[1,2,4]triazolo[4,3-a]pyridine-3-thiol

HRID 1925107Notes

Reaction equation

HRID 1925107 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][NH2:9])=[N:6][CH:7]=1.N(C1C=CC=C(C)C=1)=[C:11]=[S:12].CCOCC>ClC1C=CC(Cl)=CC=1.CN1C(=O)CCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:11]([SH:12])=[N:9][N:8]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 69304m-TolylisothiocyanateHCID 115356995-Bromo-2-hydrazinopyridine

Product 1

HCID 1785279206-Bromo-[1,2,4]triazolo[4,3-a]pyridine-3-thiol

Reagents, catalysts & solvents 2

HCID 46851,4-DichlorobenzeneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

To the suspended solution of 5-Bromo-2-hydrazinylpyridine (1.85 g, 10 mmol) in a mixture of 1,4-dichlorobenzene and NMP (5:1, 10 ml) was added isothiocyanato-3-methylbenzene (1.5 g 10 mmol). The mixture was stirred at rt for 5 min, 70° C. for 15 min, and then heated under microwave condition at 200° C. for 1.5 h. The mixture was poured into Ether (20 mL). Solid was filtered and the washed with ether to give title product.

Workup

  1. temperatureheated under microwave condition at 200° C. for 1.5 h
  2. filtrationSolid was filtered
  3. washthe washed with ether

Sources & evidence

ORD record
ord-25c95e2cc8314910862a38ccce5c67d6
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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