Methanethiol → 2-Amino-5-chloro-3-formyl-6-(methylthio)pyrazine

HRID 1981157Notes

Reaction equation

HRID 1981157 reaction equation
[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[N:6][C:5]([Cl:10])=[C:4](Cl)[N:3]=1.[CH3:12][SH:13].C(N(CC)CC)C>CN(C)C=O>[NH2:1][C:2]1[C:7]([CH:8]=[O:9])=[N:6][C:5]([Cl:10])=[C:4]([S:13][CH3:12])[N:3]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 8471TriethylamineHCID 133678713-Amino-5,6-dichloropyrazine-2-carbaldehyde

Product 1

HCID 134721362-Amino-5-chloro-3-formyl-6-(methylthio)pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 ml of dimethylformamide there was dissolved 2-amino-5,6-dichloro-3-formylpyrazine (384 mg; 0.002 M), and the solution was cooled in an ice bath. Through the solution there was then bubbled methanethiol gas for 2 minutes. Triethylamine was added, and more methanethiol gas was bubbled through the solution for 3 minutes. The reaction mixture was stirred in the ice bath for 30 minutes and then at room temperature for 30 minutes. The solvent and methanethiol were then removed under nitrogen atmosphere, and the residue was treated with water. The product precipitated, was filtered, and washed with water (333 mg). Elemental Analysis for C6H6N3OSCl.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. custommore methanethiol gas was bubbled through the solution for 3 minutes
  3. waitat room temperature for 30 minutes
  4. customThe solvent and methanethiol were then removed under nitrogen atmosphere
  5. additionthe residue was treated with water
  6. customThe product precipitated
  7. filtrationwas filtered
  8. washwashed with water (333 mg)

Sources & evidence

ORD record
ord-fe300df1356443ebab6c4c10cf1e2fd2
Source dataset
uspto-grants-1985_04
Patent number
US04512991

Reaction notes

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