Dimethyl Sulfoxide → HCID 53922531, compound

HRID 1613216Notes

Reaction equation

HRID 1613216 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH:5]([O:15][CH2:16][CH2:17][Cl:18])[N:6]1[CH2:10][CH2:9][NH:8][C:7]1=[N:11][N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Cl)=[CH:28][N:27]=1.CS(C)=O>O>[Cl:1][CH2:2][CH2:3][O:4][CH:5]([O:15][CH2:16][CH2:17][Cl:18])[N:6]1[CH2:10][CH2:9][N:8]([CH2:32][C:29]2[CH:30]=[CH:31][C:26]([Cl:25])=[N:27][CH:28]=2)[C:7]1=[N:11][N+:12]([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136403418HCID 136403418, compound

Product 1

HCID 53922531HCID 53922531, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

16.0 g of 1-[bis-(2-chloroethoxy)methyl]-2-nitroiminoimidazolidine, 13.0 g of anhydrous potassium carbonate, 13.0 g of 2-chloro-5-chloromethylpyridine and 70 ml of dimethyl sulfoxide were agitated at 70° 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 14.0 g of 1-[bis-(2-chloroethoxy)-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-fc77a698237642f68736baad7b99d855
Source dataset
uspto-grants-1993_03
Patent number
US05192778

Reaction notes

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