Allyl bromide → 2-(Nitromethylidene)-1-(prop-2-en-1-yl)imidazolidine

HRID 918037Notes

Reaction equation

HRID 918037 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)[CH:13]=[CH2:14].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][CH:13]=[CH2:12])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 30147632-(Nitromethylene)imidazolidine

Product 1

HCID 702512742-(Nitromethylidene)-1-(prop-2-en-1-yl)imidazolidineYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1.77 grams of a 57% by weight dispersion of sodium hydride in oil in 50 milliliters of dry dimethylformamide was added 5.16 grams of 2-(nitromethylene)imidazolidine. The mixture was cooled with an icebath, stirred and maintained under a nitrogen atmosphere. After 1.5 hours, 5.08 grams of allyl bromide was added. The mixture was stirred at about 10° for an additional hour, then allowed to warm to room temperature and poured into 400 milliliters of saturated aqueous sodium sulfate. The resulting mixture was extracted thrice with 300 milliliter portions of methylene chloride. The combined extract was dried (magnesium sulfate) and the solvent was evaporated. Addition of ether to the residue gave an oily red solid, which on recrystallization from chloroform (charcoal), gave 2.1 grams of 4 as tan crystals, melting point: 97°-98°.

Workup

  1. temperatureThe mixture was cooled with an icebath
  2. temperaturemaintained under a nitrogen atmosphere
  3. stirringThe mixture was stirred at about 10° for an additional hour
  4. extractionThe resulting mixture was extracted thrice with 300 milliliter portions of methylene chloride
  5. extractionThe combined extract
  6. dry with materialwas dried (magnesium sulfate)
  7. customthe solvent was evaporated
  8. additionAddition of ether to the residue
  9. customgave an oily red solid, which
  10. customon recrystallization from chloroform (charcoal)

Sources & evidence

ORD record
ord-8d15ab413a7b40c8afa845501234dece
Source dataset
uspto-grants-1976_07
Patent number
US03969354

Reaction notes

Loading…