Dimethyl Sulfoxide → HCID 54359763, compound

HRID 1033540Notes

Reaction equation

HRID 1033540 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[N:14][N+:15]([O-:17])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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>C(OCC)(=O)C.O>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][N:11]2[CH2:12][CH2:13][N:9]([CH:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:10]2=[N:14][N+:15]([O-:17])=[O:16])=[CH:27][N:26]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136378390HCID 136378390, compound

Product 1

HCID 54359763HCID 54359763, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture comprising 15.4 g of 1-(2,2-diphenylvinyl)-2-nitroiminoimidazolidine, 8.1 g of 2-chloro-5-chloromethylpyridine, 6.9 g of potassium carbonate and 80 ml of dimethylsulfoxide was stirred at 60° C. for 2 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried (with anhydrous MgSO4) and concentrated to give a crude product. To this was added 100 ml of ethyl acetate for recrystallization, and 13 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-(2,2-diphenylvinyl)imidazolidine was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (with anhydrous MgSO4)
  4. concentrationconcentrated
  5. customto give a crude product
  6. customfor recrystallization

Sources & evidence

ORD record
ord-3559d992986a435fad6f5c70cafb7bdc
Source dataset
uspto-grants-1994_05
Patent number
US05310920

Reaction notes

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