Sodium hydride → 4,5-Bis(4-methoxyphenyl)-2-(4-pyridylthio)imidazole

HRID 370798Notes

Reaction equation

HRID 370798 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[H-].[Na+].Cl.Cl[C:27]1[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:27]3[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=3)[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 818524-Chloropyridine hydrochlorideHCID 178489021HCID 178489021, compound

Product 1

HCID 128323724,5-Bis(4-methoxyphenyl)-2-(4-pyridylthio)imidazoleYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.12 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is dissolved in 100 ml of absolute dimethylformamide and combined with 0.6 g of sodium hydride (80% strength in white oil). The mixture is further agitated for 30 minutes, and then 1.52 g of 4-chloropyridine hydrochloride is added. The mixture is refluxed under argon for 16 hours. Then the solution is poured into 300 ml of ice water, the product is extracted with ethyl acetate, the organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is recrystallized from acetone/ether, thus obtaining 3.19 g of 4,5-bis(4-methoxyphenyl)-2-(4-pyridylthio)imidazole, mp 177°-179°.

Workup

  1. temperatureThe mixture is refluxed under argon for 16 hours
  2. extractionthe product is extracted with ethyl acetate
  3. dry with materialthe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is recrystallized from acetone/ether

Sources & evidence

ORD record
ord-274b828eecfd4b1cb2d3a329d61184c7
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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