Water → HCID 86742749, compound

HRID 1382229Notes

Reaction equation

HRID 1382229 reaction equation
[N+:1]([CH2:4][C:5](=O)[CH3:6])([O-:3])=[O:2].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][NH2:19])=[CH:11][N:10]=1.O>C1(C)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][NH:19][C:5]([CH3:6])=[CH:4][N+:1]([O-:3])=[O:2])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 662962-Propanone, 1-nitro-HCID 14152404HCID 14152404, compound

Product 1

HCID 86742749HCID 86742749, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Nitroacetone (1.1 g) and N-(2-chloro-5-pyridylmethyl)-N-methylethylenediamine (2.0 g) were dissolved in toluene (60 ml), and the solution was refluxed for 3 hours in a flask equipped with a water separating device while removing water formed by the reaction. Toluene was concentrated under reduced pressure, and the remaining solid was recrystallized from ethanol to give the desired N-(2-chloro-5-pyridylmethyl)-N-methyl-N'-(1-methyl-2-nitrovinyl)ethylenediamine (2.0 g) having a melting point of 78° to 80° C.

Workup

  1. temperaturethe solution was refluxed for 3 hours in a flask
  2. customwhile removing water
  3. customformed by the reaction
  4. concentrationToluene was concentrated under reduced pressure
  5. customthe remaining solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-55cf8e985b19457d94f8dbb654d4d4d9
Source dataset
uspto-grants-1989_02
Patent number
US04806553

Reaction notes

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