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

HRID 918036노트

반응식

HRID 918036 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-33620d7304cf4b34baed9a604e7f6323
출처 데이터셋
uspto-grants-1976_07
특허 번호
US03969354

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