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

HRID 1033548Notes

Reaction equation

HRID 1033548 reaction equation
[N+:1]([N:4]=[C:5]1[NH:9][CH2:8][CH2:7][NH:6]1)([O-:3])=[O:2].[CH:10](=O)[CH2:11][CH3:12].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.O>CN(C)C=O.C(OCC)(=O)C>[CH:10]([N:6]1[CH2:7][CH2:8][NH:9][C:5]1=[N:4][N+:1]([O-:3])=[O:2])=[CH:11][CH3:12]

Participants

7

Reactant 4

HCID 527PropanalHCID 962WaterHCID 14812Phosphorus oxide (P4O10)HCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 1363783921-(1-Propenyl)-2-nitroiminoimidazolidineYield 65.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

5.0 g of 2-nitroiminoimidazolidine and 4.5 g of propionaldehyde were dissolved in 25 ml of N,N-dimethylformamide, and 4.0 g of phosphorus pentoxide was added thereto with cooling with ice over a period of 20 minutes and thereafter stirred for 10 minutes at 10° C. 20 ml of water and 20 ml of ethyl acetate were added to the reaction mixture, and the crystals thus precipitated out were filtrated and dried to give 4.3 g of 1-(1-propenyl)-2-nitroiminoimidazolidine.

Workup

  1. temperaturewith cooling with ice over a period of 20 minutes
  2. customthe crystals thus precipitated out
  3. filtrationwere filtrated
  4. customdried

Sources & evidence

ORD record
ord-e12f6ba25a354dfba10ed06cd46129f0
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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