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

HRID 462939Notes

Reaction equation

HRID 462939 reaction equation
[CH3:1][SH:2].C(N(CC)CC)C.[NH2:10][C:11]1[C:16]([C:17]#[N:18])=[N:15][C:14]([Cl:19])=[C:13](Cl)[N:12]=1>CN(C)C=O>[NH2:10][C:11]1[C:16]([C:17]#[N:18])=[N:15][C:14]([Cl:19])=[C:13]([S:2][CH3:1])[N:12]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 8471TriethylamineHCID 131930613-Amino-5,6-dichloropyrazine-2-carbonitrile

Product 1

HCID 135315112-Amino-5-chloro-3-cyano-6-(methylthio)pyrazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In dimethylformamide (1.5 ml) there was dissolved 2-amino-3-cyano-5,6-dichloropyrazine (200 mmg, 1 mM) and then cooled in an ice bath. Through the solution there was then bubbled methanethiol gas for 5-10 minutes. The reaction mixture was then stirred overnight at room temperature. Triethylamine (0.14 ml) was added, followed by stirring at room temperature for 1 hour. The reaction mixture was then placed under a nitrogen atmosphere to remove solvent and excess methanethiol. The product was passed through a silica gel column, eluting with dichloromethane. The product was recrystallized from hexane/ether (139 mg). Elemental Analysis for C6H5N4ClS: :

Workup

  1. temperaturecooled in an ice bath
  2. stirringby stirring at room temperature for 1 hour
  3. customto remove solvent and excess methanethiol
  4. washeluting with dichloromethane
  5. customThe product was recrystallized from hexane/ether (139 mg)

Sources & evidence

ORD record
ord-6b940ce108864c43bd0a6e1dfea9d145
Source dataset
uspto-grants-1985_05
Patent number
US04518599

Reaction notes

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