Thionyl Chloride → HCID 58575139, compound

HRID 1807852Notes

Reaction equation

HRID 1807852 reaction equation
[Cl:1][C:2]1[C:3]([NH:17][NH:18]C2C=CC=CC=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2.S(Cl)(Cl)=O>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([C:16]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:5][CH:6]=3)=[N:18][N:17]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[C:7]([CH3:16])[CH:6]=2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86660664HCID 86660664, compound

Product 1

HCID 58575139HCID 58575139, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.38 g of methyl 3-chloro-2-hydrazine-7-methylquinoxaline-6-carboxylate was dissolved in 30.0 mL of dichloromethane, and 7.09 g of bromo(tripyrrolidin-1-yl)phosphonium hexafluorophosphate and 5.30 mL of triethylamine were added thereto under ice-cooling, followed by stirring at room temperature overnight. A saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by stirring at room temperature for 1 hour. The precipitated solid was collected by filtration and dried under reduced pressure to obtain methyl 3-chloro-7-methyl-2-(2-phenylhydrazino)quinoxaline-6-carboxylate. The obtained methyl 3-chloro-7-methyl-2-(2-phenylhydrazino)quinoxaline-6-carboxylate was suspended in 50.0 mL of tetrahydrofuran, and 1.85 mL of thionyl chloride was added thereto at room temperature, followed by heating and refluxing overnight. The reaction liquid was left to stand at room temperature and concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 2.06 g of methyl 4-chloro-8-methyl-1-phenyl[1,2,4]triazolo[4,3-a]quinoxaline-7-carboxylate as a brown solid

Workup

  1. customat room temperature
  2. temperatureby heating
  3. temperaturerefluxing overnight
  4. customThe reaction liquid
  5. waitwas left
  6. customto stand at room temperature
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-07463942dba0492da52ab284258c4ddc
Source dataset
uspto-grants-2013_01
Patent number
US08357688B2

Reaction notes

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