Sodium thiocyanate → 3,5,6-Trichloro-2-(thiocyanatomethylthio)pyrazine

HRID 866751ノート

反応式

HRID 866751 の反応式
[Cl:1][C:2]1[C:3]([S:10][CH2:11]Cl)=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1.[S-:13][C:14]#[N:15].[Na+]>CN(C)C=O>[Cl:1][C:2]1[C:3]([S:10][CH2:11][S:13][C:14]#[N:15])=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[N:7]=1

参加物

4

反応物 2

HCID 516871Sodium thiocyanate2 回HCID 203183753,5,6-Trichloro-2-(chloromethylthio)pyrazine

生成物 1

HCID 203183853,5,6-Trichloro-2-(thiocyanatomethylthio)pyrazine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

To a solution of 4.0 grams (0.015 mole) of 3,5,6-trichloro-2-(chloromethylthio)pyrazine in 75 milliliters of dimethylformamide was added 1.6 grams (0.02 mole) of sodium thiocyanate. The reaction mixture was heated to 75° C and monitored by nuclear magnetic resonance spectroscopy. An additional 4.8 grams (0.06 mole) of sodium thiocyanate was incrementally added until the reaction was complete (5 days). The solvent was removed by evaporation under reduced pressure and the residue remaining was dissolved in a mixture of water and chloroform. Two phases formed and the aqueous phase was extracted with chloroform. The organic fractions were combined and washed with a saturated sodium bicarbonate solution followed by washing with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation and the crude 3,5,6-trichloro-2-(thiocyanatomethylthio)pyrazine product was purified by elution with chloroform from a silica gel column. The product was recovered in a yield of 0.32 grams (7.5 percent of theoretical) and melted at 90°-93° C. Upon analysis, the product was found to have carbon, hydrogen, nitrogen and sulfur contents of 25.60, 1.01, 14.29 and 22.60 percent, respectively, as compared with the theoretical contents of 25.13, 0.70, 14.66 and 22.34 percent, respectively, calculated for the above-named structure.

後処理

  1. custom(5 days)
  2. customThe solvent was removed by evaporation under reduced pressure
  3. dissolutionthe residue remaining was dissolved in a mixture of water and chloroform
  4. customTwo phases formed
  5. extractionthe aqueous phase was extracted with chloroform
  6. washwashed with a saturated sodium bicarbonate solution
  7. washby washing with a saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by evaporation
  10. customthe crude 3,5,6-trichloro-2-(thiocyanatomethylthio)pyrazine product was purified by elution with chloroform from a silica gel column
  11. customThe product was recovered in a yield of 0.32 grams (7.5 percent of theoretical) and melted at 90°-93° C

出典と根拠

ORDレコード
ord-fb64ce1607da452fb9c02cdd9f65bc80
出典データセット
uspto-grants-1978_07
特許番号
US04101546

反応ノート

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