Dimethyl Sulfoxide → HCID 54102094, compound

HRID 1587730Notes

Reaction equation

HRID 1587730 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([N: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:4]=1)[CH3:2].[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]=[N:9][C:6]3[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=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 136331478HCID 136331478, compound

Product 1

HCID 54102094HCID 54102094, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.00 g of 1-(4-ethylphenyliminomethyl)-2-nitroiminoimidazolidine, 3.00 g of 2-chloro-5-chloromethylpyridine, 4.20 g of potassium carbonate, and 10 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 give an oily residue, followed by purification with column chromatography [silica gel, eluent: hexane-ethyl acetate (1:2)] to obtain 2.70 g of 1-(2-chloropyridin-5-ylmethyl)-2-nitroimino-3-(4-ethylphenyliminomethyl)imidazolidine.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. customdried
  4. customevaporated
  5. customto give an oily residue
  6. customfollowed by purification with column chromatography [silica gel, eluent: hexane-ethyl acetate (1:2)]

Sources & evidence

ORD record
ord-79cf5040dcdd4b1a8831e2a0483a7065
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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