Thionyl Chloride → Quinoxaline-6-carbonyl chloride

HRID 2261092Notes

Reaction equation

HRID 2261092 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([Cl:16])=[O:13])=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 674813Quinoxaline-6-carboxylic acid

Product 1

HCID 2776328Quinoxaline-6-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 1 l 3 neck flask was placed Quinoxaline-6-carboxylic acid (20.2 g) in 500 ml of THF. To this solution was slowly added thionylchloride (42 ml, Seq.). The reaction mechanically stirred was warmed up to reflux and followed by HPLC quenching the sample with NH4OH. After 3 h at reflux no more starting material was present, the solvent was removed under reduced pressure and SOCl2 was chased with toluene 3 times. The solid was suspended in 100 ml EtOAc and filtered to obtain 23.47 g of a beige solid.

Workup

  1. customThe reaction
  2. temperaturewas warmed up
  3. temperatureto reflux
  4. customquenching the sample with NH4OH
  5. temperatureAfter 3 h at reflux
  6. customthe solvent was removed under reduced pressure and SOCl2
  7. filtrationfiltered

Sources & evidence

ORD record
ord-67e3ef81962f40aaba9590df9def894d
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

Loading…