Oxalyl chloride → 5-Chloropyrazine-2-carbonyl chloride

HRID 1409407Notes

Reaction equation

HRID 1409407 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([Cl:14])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 4654725-Chloropyrazinoic acid

Product 1

HCID 152157435-Chloropyrazine-2-carbonyl chlorideYield 104%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chloropyrazine-2-carboxylic acid (3.15 mmol, 500 mg) was dissolved in DCM (55 ml). Oxalyl dichloride (6.62 mmol, 841 mg) was added slowly and the resulting mixture was refluxed for 2 h. After, the reaction had stopped the mixture was concentrated. 580 mg of the title compound was obtained. 1H-NMR (400 MHz, CDCl3) δ 8.78 (d, 1H), 9.09 (d, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. concentrationwas concentrated

Sources & evidence

ORD record
ord-d770f195c12e44df99b96b5fdff06b63
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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