Chloroform → Methyl 5-chloropyrazine-2-carboxylate

HRID 1964602Notes

Reaction equation

HRID 1964602 reaction equation
O[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(Cl)(Cl)[Cl:13]>CN(C)C=O>[Cl:13][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6212ChloroformHCID 178498852HCID 178498852, compound

Product 1

HCID 406081Methyl 5-chloropyrazine-2-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Methyl 5-hydroxypyrazine-2-carboxylate (673 mg, 4.37 mmol) synthesized in Example (62a) was dissolved in phosphorous oxytrichloride (6.1 mL), and a few drops of N,N-dimethylformamide were added, followed by heating to reflux for 2 hours under nitrogen atmosphere. The reaction solution was poured into ice water, and extraction was carried out three times with chloroform (30 mL). The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 mL each), and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure to afford the desired compound (611 mg, yield 81%) as a gray solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 2 hours under nitrogen atmosphere
  3. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine (100 mL each)
  4. dry with materialsubsequently dried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bc33f746f8b646129a2720a549e8a8c6
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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