Dimethylformamide → Methyl 3,5-dichloropyrazine-2-carboxylate

HRID 917608Notes

Reaction equation

HRID 917608 reaction equation
[C:1]([C:4]1[C:9]([Cl:10])=[N:8][C:7]([Cl:11])=[CH:6][N:5]=1)([OH:3])=[O:2].[C:12](=O)([O-])O.[Na+].CI.CN(C)C=O>C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:12][O:2][C:1]([C:4]1[C:9]([Cl:10])=[N:8][C:7]([Cl:11])=[CH:6][N:5]=1)=[O:3]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 226655363,5-Dichloropyrazine-2-carboxylic acid

Product 1

HCID 22665557Methyl 3,5-dichloropyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 311Citric AcidSolvent

Procedure

A mixture of 2-carboxy-3,5-dichloropyrazine (prepared in the above (1)) 226 g, sodium hydrogen carbonate 118 mg, methyl iodide 0.5 ml and dimethylformamide 1.8 ml is stirred at room temperature for 14 hours. The mixture is diluted with a 10% aqueous citric acid solution and extracted with ethyl acetate. The combined organic layer is washed with water and an aqueous saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo to give 2-methoxycarbonyl-3,5-dichloropyrazine as a pale brown crystalline powder 245 mg. mp 60-63° C., MS(m/z): 206(M+)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer is washed with water
  3. dry with materialan aqueous saturated sodium chloride solution, dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e48f66d536b3470ca1d288c134e4244e
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

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