Water → 1-(3-Methylphenyliminomethyl)-2-nitroiminoimidazolidine

HRID 1587735Notes

Reaction equation

HRID 1587735 reaction equation
C(O[CH:4](OCC)[N:5]1[CH2:9][CH2:8][NH:7][C:6]1=[N:10][N+:11]([O-:13])=[O:12])C.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=1.C(COC)OC.O>CCOCC>[CH3:24][C:20]1[CH:19]=[C:18]([N:17]=[CH:4][N:5]2[CH2:9][CH2:8][NH:7][C:6]2=[N:10][N+:11]([O-:13])=[O:12])[CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7934m-ToluidineHCID 80711,2-DimethoxyethaneHCID 1364034191-Diethoxymethyl-2-nitroiminoimidazolidine

Product 1

HCID 1363314831-(3-Methylphenyliminomethyl)-2-nitroiminoimidazolidineYield 51.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2.0 g of 1-diethoxymethyl-2-nitroiminoimidazolidine, 0.92 g of m-toluidine, 5 ml of dimethoxyethane and 0.12 g of a boron trifluoride ether complex was heated under reflux for 1 hour. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried and condensed. Ether was added to the resultant oily residue and the resultant crystals were separated by filtration and dried to give 1.1 g of 1-(3-methylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. extractionextracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customcondensed
  7. customthe resultant crystals were separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-a8017a0832354d28a84cb41dcd8c9bb5
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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