Dimethyl Sulfoxide → HCID 86747849, compound

HRID 1033546Notes

Reaction equation

HRID 1033546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[N:15][N+:16]([O-:18])=[O:17])=[CH:4][N:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][N:21]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:12]2[CH2:13][CH2:14][N:10](/[CH:9]=[CH:8]/[C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[N:3][CH:4]=3)[C:11]2=[N:15][N+:16]([O-:18])=[O:17])=[CH:22][N:21]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136378396HCID 136378396, compound

Product 1

HCID 86747849HCID 86747849, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture comprising 6.0 g of 1{2-(2-chloropyridin-5-yl)vinyl}-2-nitroiminoimidazolidine, 8.0 g of 2-chloro-5-chloromethylpyridine, 6.8 g of potassium carbonate and 60 ml of dimethylsulfoxide was stirred at 75° C. for 2.5 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO4) and concentrated to give an oily residue. This was purified by column chromatography (silica gel, eluent: ethyl acetate) to give 3.9 of 1-(2 chloropyridin-5-ylmethyl)-2-nitroimino-3-{trans-2-(2-chloropyridin-5-yl)vinyl}imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (with anhydrous MgSO4)
  4. concentrationconcentrated
  5. customto give an oily residue
  6. customThis was purified by column chromatography (silica gel, eluent: ethyl acetate)

Sources & evidence

ORD record
ord-780a4f6ec2834c719883092efb58f657
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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