Dimethyl Sulfoxide → HCID 54121921, compound

HRID 258119Notes

Reaction equation

HRID 258119 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][N:9]1[CH2:13][CH2:12][NH:11][C:10]1=[N:14][N+:15]([O-:17])=[O:16])[CH2:5][CH3:6])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][N:26]=1.CS(C)=O>O>[CH2:1]([O:3][CH:4]([O:7][CH2:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:31][C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[N:26][CH:27]=2)[C:10]1=[N:14][N+:15]([O-:17])=[O:16])[CH2:5][CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136403417HCID 136403417, compound

Product 1

HCID 54121921HCID 54121921, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

15.0 g of 1-(1-ethoxy-1-propoxy)methyl-2-nitroiminoimidazolidine, 11.6 g of anhydrous potassium carbonate, 11.3 g of 2-chloro-5-chloromethylpyridine and 60 ml of dimethyl sulfoxide were agitated at 75° C. for 1 hour. The reaction mixture was poured into water, and extracted with ethyl acetate. After washing with water, the extract was dried with anhydrous sodium sulfate, after which the solvent was distilled off under reduced pressure. The resultant oily residue was purified by column chromatography [silica gel, eluant hexane/ethyl acetate (1:2)] to give 4.7 g of 1-(1-ethoxy-1-propoxy)methyl-2-nitroimino-3-(2-chloropyridin-5-ylmethyl)imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing with water
  3. dry with materialthe extract was dried with anhydrous sodium sulfate
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. customThe resultant oily residue was purified by column chromatography [silica gel, eluant hexane/ethyl acetate (1:2)]

Sources & evidence

ORD record
ord-163d11dfbfbf453e82ea93faa9e07bf7
Source dataset
uspto-grants-1993_11
Patent number
US05264584

Reaction notes

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