Thionyl Chloride → HCID 67395840, compound

HRID 869720Notes

Reaction equation

HRID 869720 reaction equation
[CH3:1][C:2]1[C:3]([C:10]([O-:12])=[O:11])=[N:4][C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=1.S(Cl)(Cl)=O.[C:17](=O)(O)[O-].[Na+]>CO>[CH3:1][C:2]1[C:3]([C:10]([O:12][CH3:17])=[O:11])=[N:4][C:5]([CH3:9])=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86674521HCID 86674521, compound

Product 1

HCID 67395840HCID 67395840, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,5,6-trimethylpyrazine-2-carboxylate (5.38 g, 30.0 mmol) in methanol (90 mL) was added thionyl chloride (3.70 mL, 51.0 mmol) was added at 0° C. After being stirred at room temperature overnight, the reaction mixture was poured into saturated aqueous sodium bicarbonate. The mixture was extracted with ethyl acetate and the organic layer was washed with water and saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo to give methyl 3,5,6-trimethylpyrazine-2-carboxylate. MS (APCI): m/z 181 (M+H).

Workup

  1. additionwas added at 0° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5491f47572e048a3959d6b1d9a87ec6c
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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