Dimethyl Sulfoxide → HCID 57208188, compound

HRID 1033539Notes

Reaction equation

HRID 1033539 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[N:16][N+:17]([O-:19])=[O:18])[CH:5]=[CH:6][C:7]=1[Cl:8].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][N:13]2[CH2:14][CH2:15][N:11]([CH:10]=[CH:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:12]2=[N:16][N+:17]([O-:19])=[O:18])=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 137226506HCID 137226506, compound

Product 1

HCID 57208188HCID 57208188, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 7.0 g of 1-{2-(3,4-dichlorophenyl)vinyl}-2-nitroiminoimidazolidine, 7.5 g of 2-chloro-5-chloromethylpyridine, 6.4 g of potassium carbonate and 50 ml of dimethylsulfoxide 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 MgS04) and concentrated o give an oily residue. This was purified by column chromatography (silica gel, eluent: ethyl acetate) to give 5.7 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-(3,4-dichlorphenylvinyl) -imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried (with anhydrous MgS04)
  4. concentrationconcentrated
  5. customo give an oily residue
  6. customThis was purified by column chromatography (silica gel, eluent: ethyl acetate)

Sources & evidence

ORD record
ord-303064937b4043efa172e1bdadb2e366
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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