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

HRID 2164761Notes

Reaction equation

HRID 2164761 reaction equation
[CH3:1][SH:2].C(N(CC)CC)C.O.[NH2:11][C:12]1[C:17]([CH:18]=[O:19])=[N:16][C:15]([Cl:20])=[C:14](Cl)[N:13]=1>CN(C)C=O>[NH2:11][C:12]1[C:17]([CH:18]=[O:19])=[N:16][C:15]([Cl:20])=[C:14]([S:2][CH3:1])[N:13]=1

Participants

6

Reactant 4

HCID 878Methanethiol3×HCID 962WaterHCID 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 6228DimethylformamideSolvent2×

Procedure

In 3 ml of dimethylformamide there was dissolved 2-amino-5,6-dichloro-3-formylpyrazine prepared as described in Example 1, Steps A and B. The solution was cooled in an ice bath, and there was then bubbled therethrough methane thiol, for 2 minutes followed by addition of triethylamine (223 mg; 2.2 mMol), followed by methane thiol addition for another 3 minutes. The reaction mixture was stirred for 30 minutes at the ice bath temperature and for 30 minutes at room temperature. The methane thiol and dimethylformamide were then blown off, the residue was treated with water, and the product precipitated, was filtered and washed (333 mg). Elemental Analysis for C6H6N3OSCl:

Workup

  1. customprepared
  2. temperatureThe solution was cooled in an ice bath
  3. customthere was then bubbled
  4. customthe product precipitated
  5. filtrationwas filtered
  6. washwashed (333 mg)

Sources & evidence

ORD record
ord-17972c1638ef4180b6ca3df4db1a09b4
Source dataset
uspto-grants-1985_03
Patent number
US04507299

Reaction notes

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