Dimethyl Sulfoxide → HCID 53714312, compound

HRID 1033545Notes

Reaction equation

HRID 1033545 reaction equation
[CH2:1]([S:3][CH:4]=[CH:5][N:6]1[CH2:10][CH2:9][NH:8][C:7]1=[N:11][N+:12]([O-:14])=[O:13])[CH3:2].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Cl)=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:8]2[CH2:9][CH2:10][N:6]([CH:5]=[CH:4][S:3][CH2:1][CH3:2])[C:7]2=[N:11][N+:12]([O-:14])=[O:13])=[CH:18][N:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136378395HCID 136378395, compound

Product 1

HCID 53714312HCID 53714312, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 8.0 g of 1-(2-ethylthiovinyl)-2-nitroiminoimidazolidine, 7.2 g of 2-chloro-5-chloromethylpyridine, 20.0 g of potassium carbonate .and 30 ml of dimethylsulfoxide was stirred at 60° C. for 30 minutes. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO) and concentrated to give an oily residue. This was purified by column chromatography silica gel, eluent: ethyl acetate/hexane 4/1) to give 8.3 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-(2-ethylthiovinyl)imidazolidine.

Workup

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

Sources & evidence

ORD record
ord-d5c80655f5cb4e84b997c80cefa0a667
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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