O-Xylene → 8-Chloro-(1,2,4)triazolo(4,3-a)pyrazine

HRID 552813Notes

Reaction equation

HRID 552813 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][NH2:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH:10](OCC)(OCC)OCC.C1(C)C(C)=CC=CC=1>C(OCC)C>[Cl:1][C:2]1[C:3]2[N:4]([CH:10]=[N:9][N:8]=2)[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 31214Ethyl orthoformateHCID 3214302-Chloro-3-hydrazinopyrazine

Product 1

HCID 125826128-Chloro-(1,2,4)triazolo(4,3-a)pyrazineYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(3-chloropyrazin-2-yl)hydrazine (0.90 g, 62 mmol), triethyl orthoformate (2.3 mL), 14 mmol), and dry xylene (15 mL) was refluxed with stirring for 2 h. The mixture was brought to RT, diethyl ether was added and the suspension was filtered. The solid collected was washed with diethyl ether to afford 8-chloro-[1,2,4]triazolo[4,3-a]pyrazine (0.60 g, 62% yield). MS m/z: 155.0 (M+1).

Workup

  1. temperaturewas refluxed
  2. customwas brought to RT
  3. filtrationthe suspension was filtered
  4. customThe solid collected
  5. washwas washed with diethyl ether

Sources & evidence

ORD record
ord-2146adaae74b4bceb13b65a3f10e0abf
Source dataset
uspto-grants-2011_05
Patent number
US07951838B2

Reaction notes

Loading…