Dimethyl Sulfoxide → HCID 54121921, compound

HRID 1613215Notes

Reaction equation

HRID 1613215 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-9a5c22dbda74414f9e2e8eb781447196
Source dataset
uspto-grants-1993_03
Patent number
US05192778

Reaction notes

Loading…