Dimethyl Sulfoxide → HCID 57293194, compound

HRID 1033541Notes

Reaction equation

HRID 1033541 reaction equation
[F:1][C:2]([F:23])([F:22])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][N:13]2[CH2:17][CH2:16][NH:15][C:14]2=[N:18][N+:19]([O-:21])=[O:20])=[CH:7][CH:6]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Cl)=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:15]2[CH2:16][CH2:17][N:13]([CH:12]=[CH:11][C:8]3[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:22])[F:23])=[CH:10][CH:9]=3)[C:14]2=[N:18][N+:19]([O-:21])=[O:20])=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136378391HCID 136378391, compound

Product 1

HCID 57293194HCID 57293194, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 5.0 g of 1-{4-(2,2,2-trifluoroethoxy)phenylvinyl}-2-nitroiminoimidazolidine, 5.8 g of 2-chloro-5-chloromethylpyridine, 8.4 g of potassium carbonate and 30 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 MgSO4) and concentrated to give an oily residue. This was purified by column chromatography (silica gel, eluent: ethyl acetate/hexane=4/1) to give 4.9 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-{4-(2,2,2-trifluoroethoxy)phenylvinyl}-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/hexane=4/1)

Sources & evidence

ORD record
ord-ed56ac5bb0d540d38ca214ef5fa9e64b
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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