Propargyl bromide → 2-(Nitromethylidene)-1-(prop-2-yn-1-yl)imidazolidine

HRID 1414897ノート

反応式

HRID 1414897 の反応式
[H-].[Na+].[N+:3]([CH:6]=[C:7]1[NH:11][CH2:10][CH2:9][NH:8]1)([O-:5])=[O:4].[CH2:12](Br)[C:13]#[CH:14].S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C)C=O>[N+:3]([CH:6]=[C:7]1[NH:11][CH2:10][CH2:9][N:8]1[CH2:14][C:13]#[CH:12])([O-:5])=[O:4]

参加物

6

反応物 4

HCID 7842Propargyl bromideHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 30147632-(Nitromethylene)imidazolidine

生成物 1

HCID 714446262-(Nitromethylidene)-1-(prop-2-yn-1-yl)imidazolidine収率 46.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

An ice-cooled mixture of 50 milliliters of dry dimethylformamide and 1.77 grams of a 57% by weight dispersion of sodium hydride in mineral oil, maintained under nitrogen atmosphere, was treated with 5.16 grams of 2-(nitromethylene)imidazolidine. After stirring for 1 hour, 7.97 grams of propargyl bromide was added. The mixture was stirred at 10° for an additional hour, allowed to warm to room temperature, and poured into 400 milliliters of saturated aqueous sodium sulfate. The product was extracted with three 300-milliliter portions of methylene chloride. The combined extract was dried with magnesium sulfate and the solvent was evaporated. Addition of ether to the residual oil gave a solid which was recrystallized from chloroform (charcoal) to give 3.1 grams of 3, as tan crystals, melting point: 146°-147° C.

後処理

  1. temperaturemaintained under nitrogen atmosphere
  2. stirringThe mixture was stirred at 10° for an additional hour
  3. extractionThe product was extracted with three 300-milliliter portions of methylene chloride
  4. extractionThe combined extract
  5. dry with materialwas dried with magnesium sulfate
  6. customthe solvent was evaporated
  7. additionAddition of ether to the residual oil
  8. customgave a solid which
  9. customwas recrystallized from chloroform (charcoal)

出典と根拠

ORDレコード
ord-3ca61d690e804fdcb477c4c16e57453e
出典データセット
uspto-grants-1977_01
特許番号
US04002765

反応ノート

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