Glycidol → 6-(2-Oxiranylmethoxy)[1,2,4]triazolo[4,3-b]pyridazine

HRID 397553

反応式

HRID 397553 の反応式
[O:1]1[CH2:3][CH:2]1[CH2:4][OH:5].Cl[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][N:15]=2)[N:12]=1.[H-].[Na+]>CN(C)C=O>[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:7]1[CH:8]=[CH:9][C:10]2[N:11]([CH:13]=[N:14][N:15]=2)[N:12]=1

参加物

5

反応物 3

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazine

生成物 1

HCID 230003166-(2-Oxiranylmethoxy)[1,2,4]triazolo[4,3-b]pyridazine収率 32.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

12.0 g of 2-oxiranylmethanol and 2.50 g of 6-chloro[1,2,4]triazolo[4,3-b]pyridazine were dissolved in 40 ml of N,N-dimethylformamide; under ice cooling, 713 mg of 60% oily sodium hydride was added, followed by stirring at room temperature for 30 minutes. After cold saline was added, the reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1) and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with ethyl acetate-methanol (10:1). The desired fraction was collected and concentrated under reduced pressure; the precipitated crystal was washed with diethyl ether and dried to yield 1.02 g of the title compound.

後処理

  1. additionAfter cold saline was added
  2. extractionthe reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialdried over magnesium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. washeluted with ethyl acetate-methanol (10:1)
  6. customThe desired fraction was collected
  7. concentrationconcentrated under reduced pressure
  8. washthe precipitated crystal was washed with diethyl ether
  9. customdried

出典と根拠

ORDレコード
ord-8957a2a462814b4bae3c9e5dff4a92b5
出典データセット
uspto-grants-2003_08
特許番号
US06610694B1

関連ノート

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