Phosphorus oxychloride → HCID 86662009, compound

HRID 1422803Notes

Reaction equation

HRID 1422803 reaction equation
[CH3:1][S:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=O)[NH:10]2)=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:16])=O>ClCCl>[Cl:16][C:9]1[CH:8]=[N:7][C:6]2[C:11](=[CH:12][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66746858HCID 66746858, compound

Product 1

HCID 86662009HCID 86662009, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-methylsulfanyl-1H-quinoxalin-2-one (9.23 g, 48.0 mmol, 1.0 eq) in phosphorus oxychloride (36 mL, 384.0 mmol, 8.0 eq) is heated under reflux for 30 minutes. Then the reaction mixture is cooled down to room temperature and the solvent is evaporated. The residue is poured into ice water, the resulting mixture is basified with saturated sodium hydrogen carbonate to pH=8˜9 and extracted with ethyl acetate (3×50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:dichloromethane, 4:1 to 1:1, v/v) to afford 2-chloro-7-methylsulfanyl-quinoxaline as a green solid (3.41 g, 33% yield).

Workup

  1. temperatureunder reflux for 30 minutes
  2. customthe solvent is evaporated
  3. additionThe residue is poured into ice water
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude product that
  9. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-4a96c018db424d30823f54c3805472d1
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

Loading…