Propargyl bromide → 2-(Nitromethylidene)-1-(prop-2-yn-1-yl)imidazolidine
Reaction equation
[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]Participants
Procedure
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.
Workup
- temperaturemaintained under nitrogen atmosphere
- stirringThe mixture was stirred at 10° for an additional hour
- extractionThe product was extracted with three 300-milliliter portions of methylene chloride
- extractionThe combined extract
- dry with materialwas dried with magnesium sulfate
- customthe solvent was evaporated
- additionAddition of ether to the residual oil
- customgave a solid which
- customwas recrystallized from chloroform (charcoal)
Sources & evidence
- ORD record
- ord-33620d7304cf4b34baed9a604e7f6323
- Source dataset
- uspto-grants-1976_07
- Patent number
- US03969354
Reaction notes
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