Methanol → 2-Iodo-6-methoxypyrazine

HRID 1110335Notes

Reaction equation

HRID 1110335 reaction equation
[I:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4](I)[N:3]=1.[CH3:9][O-:10].[Na+].CO>O>[I:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:10][CH3:9])[N:3]=1

Participants

5

Procedure

2,6-Diiodopyrazine (5.0 g, 15 mmol) was added to a solution of sodium methoxide in methanol (prepared from sodium (0.35 g, 15 mmol) and methanol (40 ml)) and the mixture was heated at reflux temperature for 1 hour. After cooling, the solution was diluted with water (200 ml) and extracted with diethylether (3×100 ml). The combined extracts were washed with water, dried over magnesium sulphate and concentrated under reduced pressure to give the product as a white solid (3.5 g, 100%) m. pt. 35.7-37.2

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureAfter cooling
  4. extractionextracted with diethylether (3×100 ml)
  5. washThe combined extracts were washed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1cca32c35194c228b6908ac057c6531
Source dataset
uspto-grants-1990_12
Patent number
US04975112

Reaction notes

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