Dimethyl Sulfoxide → HCID 53827712, compound

HRID 1587733Notes

Reaction equation

HRID 1587733 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[CH:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[N:17][N+:18]([O-:20])=[O:19])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28]Cl)=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][N:14]2[CH2:15][CH2:16][N:12]([CH:11]=[N:10][C:7]3[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=3)[C:13]2=[N:17][N+:18]([O-:20])=[O:19])=[CH:24][N:23]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136331481HCID 136331481, compound

Product 1

HCID 53827712HCID 53827712, compoundYield 39.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.00 g of 1-(4-acetylphenyliminomethyl)-2-nitroiminoimidazolidine, 2.12 g of 2-chloro-5-chloromethylpyridine, 3.01 g of potassium carbonate, and 7 ml of DMSO was agitated at 60° C. for 1 hour. The reaction mixture was poured into water, extracted with ethyl acetate, washed with water, dried and evaporated to obtain an oily residue. To the resultant oily residue was added ethyl acetate, followed by separation of the resultant crystals by filtration and drying to give 1.73 g of 1-(2-chloropyridine-5-ylmethyl)-2-nitroimino-3-(4-acetylphenyliminomethyl)imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customto obtain an oily residue
  6. customfollowed by separation of the resultant crystals
  7. filtrationby filtration
  8. customdrying

Sources & evidence

ORD record
ord-a35b3aad1e0041348953f3099ae7ad29
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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