Dimethyl Sulfoxide → 1-(2-Chloropyridin-5-ylmethyl)-2-nitroimino-3-(1propenyl)imidazolidine

HRID 1033542Notes

Reaction equation

HRID 1033542 reaction equation
[CH:1]([N:4]1[CH2:8][CH2:7][NH:6][C:5]1=[N:9][N+:10]([O-:12])=[O:11])=[CH:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Cl)=[CH:26][N:25]=1>O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:6]2[CH2:7][CH2:8][N:4]([CH:1]=[CH:2][CH3:3])[C:5]2=[N:9][N+:10]([O-:12])=[O:11])=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 1363783921-(1-Propenyl)-2-nitroiminoimidazolidine

Product 1

HCID 538530701-(2-Chloropyridin-5-ylmethyl)-2-nitroimino-3-(1propenyl)imidazolidineYield 82.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 6.0 g of 1-(1-propenyl)-2nitroiminoimidazolidine, 7.0 g of potassium carbonate, 70 ml of DMSO and 7.4 g of 2-chloro-5-chloromethylpyridine was stirred at 60° C. for one hour. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO4) and concentrated to give an oily residue. This was purified by column chromatography (silica gel, eluent: ethyl acetate/hexane=2/1) to give 8.6 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino -3- (1propenyl)imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (with anhydrous MgSO4)
  4. concentrationconcentrated
  5. customto give an oily residue
  6. customThis was purified by column chromatography (silica gel, eluent: ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-7fd2b7f3e87b45f7bfe424c6333d3eee
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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