Oxalyl chloride → HCID 89498529, compound

HRID 336585Notes

Reaction equation

HRID 336585 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:10])=O)[NH:5][C:6]=1[CH3:7].C(Cl)(=O)C(Cl)=O>CN(C=O)C.N1C=CC=CC=1.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:8]#[N:10])[NH:5][C:6]=1[CH3:7]

Participants

6

Reactant 2

HCID 65578Oxalyl chlorideHCID 89498250HCID 89498250, compound

Product 1

HCID 89498529HCID 89498529, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of EXAMPLE 23C (7.89 g) in DMF (80 mL) and pyridine (5 mL) at 0° C. was added dropwise oxalyl chloride (5.52 mL). The mixture was stirred at 0° C. for 30 minutes and ice-water was added to quench the reaction. The resulting mixture was diluted with ethyl acetate and washed with aqueous NaHCO3 and water extensively. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by flash column, eluting with dichloromethane to provide the title compound.

Workup

  1. customto quench
  2. customthe reaction
  3. washwashed with aqueous NaHCO3 and water extensively
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-9c48b600c22b47dfbbf475b5207a1234
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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