Phosphorus oxychloride → 1192756-62-9

HRID 72125Notes

Reaction equation

HRID 72125 reaction equation
O=[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[NH:3]1.O=P(Cl)(Cl)[Cl:16]>CN(C=O)C.C(Cl)Cl>[Cl:16][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]#[N:13])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 451217302-Hydroxyquinoxaline-6-carbonitrile

Product 1

HCID 582548171192756-62-9

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Oxo-1,2-dihydroquinoxaline-6-carbonitrile was suspended in POCl3 (25 mL) and DMF (10 drops) was added. The mixture was heated at 100° C. for 2 h, cooled and concentrated under reduced pressure to leave a black residue. The residue was dissolved in CH2Cl2 (200 mL), washed with satd aq NaHCO3 (25 mL) and brine (25 mL) and dried over Na2SO4. Removal of the solvent left an off white solid (4.50 g). A 0.50-g portion was purified by chromatography on a 40-g silica gel cartridge eluted with a 0-50% EtOAc in hexanes gradient to afford 2-chloroquinoxaline-6-carbonitrile (118 mg). LC-MS Method 1 tR=1.42 min, m/z=190.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. customto leave a black residue
  4. washwashed with satd aq NaHCO3 (25 mL) and brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. waitleft an off white solid (4.50 g)
  8. customA 0.50-g portion was purified by chromatography on a 40-g silica gel cartridge
  9. washeluted with a 0-50% EtOAc in hexanes gradient

Sources & evidence

ORD record
ord-fe278a7b3773404c9d65c4f59614fe21
Source dataset
uspto-grants-2014_09
Patent number
US08828985B2

Reaction notes

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