Thiophosgene → 2-Isothiocyanato-3,5-dimethylpyrazine

HRID 1628509ノート

反応式

HRID 1628509 の反応式
[C:1](Cl)(Cl)=[S:2].[CH3:5][C:6]1[C:7]([NH2:13])=[N:8][CH:9]=[C:10]([CH3:12])[N:11]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:13]([C:7]1[C:6]([CH3:5])=[N:11][C:10]([CH3:12])=[CH:9][N:8]=1)=[C:1]=[S:2]

参加物

5

反応物 2

HCID 10040ThiophosgeneHCID 27747642-Amino-3,5-dimethylpyrazine

生成物 1

HCID 866328962-Isothiocyanato-3,5-dimethylpyrazine収率 33%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒2 回

反応条件

温度
0 °C

実験手順

Thiophosgene (1.59 mL, 20.9 mmol) was added dropwise to a stirred mixture of 3,5-dimethylpyrazin-2-amine (1.98 g, 16.1 mmol) in tetrahydrofuran (20 mL) and saturated aqueous sodium hydrogen carbonate (20 mL) at 0° C., and the mixture was stirred at 0° C. for 1 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a brown solid (866 mg, 5.24 mmol, 33%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  7. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-b9cfd411a63444eeb390ff67b153d730
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

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