Propargyl bromide → 1-(Prop-2-yn-1-yl)imidazolidin-2-one

HRID 1170426ノート

反応式

HRID 1170426 の反応式
[CH2:1]1[NH:6][C:4](=[O:5])[NH:3][CH2:2]1.[CH2:7]([Li])[CH2:8][CH2:9]C.CCCCCC.BrCC#C.S(=O)(=O)(O)[O-].[K+]>O1CCCC1>[CH2:9]([N:3]1[CH2:2][CH2:1][NH:6][C:4]1=[O:5])[C:8]#[CH:7]

参加物

6

反応物 4

HCID 7842Propargyl bromideHCID 84532-ImidazolidinoneHCID 516920Potassium bisulfateHCID 178418244HCID 178418244、化合物

生成物 1

HCID 156696571-(Prop-2-yn-1-yl)imidazolidin-2-one収率 24%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a suspension of ethylene urea (592 mg, 6.88 mmol) in tetrahydrofuran (15 mL) was added dropwise butyl lithium/hexane solution (2.7 mL, 13.6 mmol) at 0° C. under nitrogen. Thereto was added 3-bromopropyne (410 mg, 6.88 mmol), and the mixture was stirred at 60° C. for 3 hours. Thereto was added 5% aqueous potassium bisulfate solution, and the mixture was extracted with ethyl acetate, dried over magnesium sulfate, and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (ethyl acetate/hexane 1/1) to give the titled compound (202 mg, 24%).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane 1/1)

出典と根拠

ORDレコード
ord-e8b54dab38d047f7b31bfa9daba23259
出典データセット
uspto-grants-2010_11
特許番号
US07825155B2

反応ノート

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