Thiophosgene → 5-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidine

HRID 1628513ノート

反応式

HRID 1628513 の反応式
[C:1](Cl)(Cl)=[S:2].[CH3:5][O:6][C:7]1[N:12]=[C:11]([CH3:13])[C:10]([NH2:14])=[C:9]([CH3:15])[N:8]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[N:14]([C:10]1[C:9]([CH3:15])=[N:8][C:7]([O:6][CH3:5])=[N:12][C:11]=1[CH3:13])=[C:1]=[S:2]

参加物

5

反応物 2

HCID 10040ThiophosgeneHCID 687393852-Methoxy-4,6-dimethylpyrimidin-5-amine

生成物 1

HCID 866328935-Isothiocyanato-2-methoxy-4,6-dimethylpyrimidine収率 88%

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 (1.8 mL, 23.6 mmol) was added dropwise to a stirred mixture of 2-methoxy-4,6-dimethylpyrimidin-5-amine (2.82 g, 18.4 mmol) in tetrahydrofuran (25 mL) and saturated aqueous sodium hydrogen carbonate (25 mL) at 0° C., and the mixture was stirred at 0° C. for 40 minutes. 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 washed with diisopropyl ether/n-hexane to give the title compound as a pale yellow powder (3.16 g, 16.2 mmol, 88%).

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. washThe residue was washed with diisopropyl ether/n-hexane

出典と根拠

ORDレコード
ord-e736bd3fcc62484c91a6ac605e8f2559
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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