Hydrochloric Acid → 4,5-Bis(4-methoxyphenyl)-2-(2-fluorophenylthio)imidazole

HRID 1995198Notes

Reaction equation

HRID 1995198 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1N.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:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[F:1])[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 95842-FluoroanilineHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 178489021HCID 178489021, compound

Product 1

HCID 128323074,5-Bis(4-methoxyphenyl)-2-(2-fluorophenylthio)imidazoleYield 33.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

At 0° a diazonium salt solution prepared from 2.5 g of 2-fluoroaniline, 1.58 g of sodium nitrite, and 10 ml of 6 N 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 2 N sodium hydroxide solution, and 1.45 g of powdered copper. The solution develops a reddish brown color under nitrogen evolution. The mixture is further stirred for 3 hours, 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 subjected to column chromatography on 500 g of silica gel. Elution with acetone/hexane 2:3 yields 2.71 g of 4,5-bis(4-methoxyphenyl)-2-(2-fluorophenylthio)imidazole having a melting point of 195° after recrystallization from hot diisopropyl ether.

Workup

  1. concentrationconcentrated under vacuum
  2. dry with materialThe organic solution is dried over sodium sulfate
  3. concentrationconcentrated to dryness under vacuum
  4. washElution with acetone/hexane 2:3

Sources & evidence

ORD record
ord-4bb6814159784cbc9def6b1b18f0da46
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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