Methanol → 3,5,6-Trichloro-2-methylthiopyrazine

HRID 866749Notes

Reaction equation

HRID 866749 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[N:4][C:3]=1Cl.[Na+].[SH-:12].O.[CH3:14]O>>[Cl:1][C:2]1[C:3]([S:12][CH3:14])=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 28015Sodium hydrosulfideHCID 311820Tetrachloropyrazine

Product 1

HCID 203183743,5,6-Trichloro-2-methylthiopyrazine

Procedure

A solution was prepared by dissolving 25 grams (0.115 mole) of tetrachloropyrazine in 300 milliliters of methanol. To this solution was added over a 90 minute period, a solution of 115 milliliters of ~1.0 molar sodium mercaptide in methanol. The temperature was maintained below 20° C during the addition. The reaction mixture was stirred at room temperature overnight and thereafter poured into 400 milliliters of water. The precipitate which formed was removed by filtration and recrystallized from hexane. The 3,5,6-trichloro-2-methylthiopyrazine product was recovered in a yield of 7.11 grams, 27 percent of theoretical, and melted at 45°-47° C.

Workup

  1. customA solution was prepared
  2. additionTo this solution was added over a 90 minute period
  3. temperatureThe temperature was maintained below 20° C during the addition
  4. customThe precipitate which formed
  5. customwas removed by filtration
  6. customrecrystallized from hexane
  7. customThe 3,5,6-trichloro-2-methylthiopyrazine product was recovered in a yield of 7.11 grams, 27 percent of theoretical, and melted at 45°-47° C.

Sources & evidence

ORD record
ord-4414d70699e643b4bac9a2c312fea4da
Source dataset
uspto-grants-1978_07
Patent number
US04101546

Reaction notes

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