1,2-Dibromoethane → HCID 89853797、化合物

HRID 931158ノート

反応式

HRID 931158 の反応式
[H-].[Na+].[N:3]1([CH2:8][C:9]#[N:10])[CH:7]=[CH:6][CH:5]=[N:4]1.Br[CH2:12][CH2:13]Br.[Cl-].[NH4+]>CS(C)=O>[N:3]1([C:8]2([C:9]#[N:10])[CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=[N:4]1

参加物

6

反応物 4

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 70178431H-pyrazol-1-ylacetonitrile

生成物 1

HCID 89853797HCID 89853797、化合物収率 28%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Sodium hydride (4.65 g, 121 mmol, 60% oil dispersion) was washed with petroleum ether under a nitrogen atmosphere. The supernatant was removed after the suspension settled in order to remove the mineral oil. Then a solution of 2-(1H-pyrazol-1-yl)acetonitrile (3 g, 27 mmol) and 1,2-dibromoethane (6.98 mL, 81 mmol) in dimethylsulfoxide (90 mL) was added at 20° C. over a period of 40 min. The reaction mixture was stirred at room temperature for 5 d. A saturated aqueous solution of ammonium chloride was added and the mixture was stirred at 0° C. for 15 min, extracted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether) to afford 1-(1H-pyrazol-1-yl)cyclopropanecarbonitrile (1 g, 28%).

後処理

  1. customThe supernatant was removed after the suspension
  2. customto remove the mineral oil
  3. stirringthe mixture was stirred at 0° C. for 15 min
  4. extractionextracted with diethyl ether
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting crude was purified via column chromatography (100-200 mesh silica gel, 5-12% ethyl acetate in petroleum ether)

出典と根拠

ORDレコード
ord-27fa49f0335c461f93cc223099020f82
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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