Hydrochloric Acid → 2-[(4-Fluorophenyl)sulfanyl]-4,5-bis(4-methoxyphenyl)-1H-imidazole

HRID 370769Notes

Reaction equation

HRID 370769 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5](N)=[CH:4][CH:3]=1.N([O-])=O.[Na+].Cl.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[C:24]([SH:35])[NH:25][C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:18][CH:17]=1.[OH-].[Na+]>CN(C)C=O.[Cu]>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([C:26]2[N:25]=[C:24]([S:35][C:5]3[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=3)[NH:23][C:22]=2[C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 97314-FluoroanilineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, compound

Product 1

HCID 128323082-[(4-Fluorophenyl)sulfanyl]-4,5-bis(4-methoxyphenyl)-1H-imidazoleYield 38%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

At 0° a diazonium salt solution prepared from 2.5 g of 4-fluoroaniline, 1.58 g of sodium nitrite, and 10 ml of 6N hydrochloric acid is added dropwise to a solution of 6.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole in a mixture of 240 ml of dimethylformamide, 10 ml of 2N sodium hydroxide solution, and 1.45 g of pulverized copper. The solution assumes a reddish brown color under evolution of nitrogen. The mixture is agitated for another 3 hours, the solution is concentrated under vacuum, and the residue is distributed between water and ethyl acetate. The organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is chromatographed over a column on 500 g of silica gel. Elution with acetone/hexane 2:3 yields 3.09 g of 4,5-bis(4-methoxyphenyl)-2-(4-fluorophenylthio)imidazole, mp 106° after recrystallization from hot diisopropyl ether/methylene chloride.

Workup

  1. concentrationthe solution is concentrated under vacuum
  2. dry with materialThe organic solution is dried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. customThe residue is chromatographed over a column on 500 g of silica gel
  5. washElution with acetone/hexane 2:3

Sources & evidence

ORD record
ord-f6962141a2bf4f089fbdf564752e4f0e
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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