Propanal → 1-(1-Propenyl)-2-nitroiminoimidazolidine

HRID 1033547Notes

Reaction equation

HRID 1033547 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.[CH:15](=O)[CH2:16][CH3:17]>O>[CH:15]([N:6]1[CH2:7][CH2:8][NH:9][C:5]1=[N:4][N+:1]([O-:3])=[O:2])=[CH:16][CH3:17]

Participants

5

Reactant 3

HCID 527PropanalHCID 24813Phosphorus oxychlorideHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1363783921-(1-Propenyl)-2-nitroiminoimidazolidineYield 32.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 4.0 g of 2-nitroiminoimidazolidine, 20 ml of 1,3-dimethyl-2imidazolidine, 7.5 g of phosphorus oxychloride and 2.7 g of propionaldehyde was stirred for 30 minutes at room temperature. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO4) and concentrated. The crystals thus precipitated out were sludged with ethyl acetate, filtrated and dried to give 1.7 g of 1-(1-propenyl)-2-nitroiminoimidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (with anhydrous MgSO4)
  4. concentrationconcentrated
  5. customThe crystals thus precipitated out
  6. filtrationfiltrated
  7. customdried

Sources & evidence

ORD record
ord-98bc24d177894b46877e9ca5b36e629b
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

Loading…