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

HRID 1995233Notes

Reaction equation

HRID 1995233 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+].[H][H].[F:27][C:28]([F:37])([F:36])[C:29]1[CH:35]=[CH:34][C:32](N)=[CH:31][CH:30]=1.N([O-])=O.[Na+].Cl>CN(C)C=O.[Cu]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][C:32]3[CH:34]=[CH:35][C:29]([C:28]([F:37])([F:36])[F:27])=[CH:30][CH:31]=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

9

Reactant 6

HCID 313Hydrochloric AcidHCID 99644-(Trifluoromethyl)anilineHCID 24758Sodium hydrideHCID 23668193Sodium NitriteHCID 178418361HCID 178418361, compoundHCID 178489021HCID 178489021, compound

Product 1

HCID 128323054,5-Bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazoleYield 37.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Procedure

6.25 g of 4,5-bis(4-methoxyphenyl)-2-mercaptoimidazole is dissolved in 150 ml of absolute dimethylformamide and combined with 0.60 g of sodium hydride (80% in oil). After the evolution of hydrogen has ceased, the solution is cooled to 0°, combined with a pinch of powdered copper, and then a diazonium salt solution, cooled to 0° and prepared from 3.26 g of 4-trifluoromethylaniline (99%), 1.38 g of sodium nitrite, as well as 10 ml of 6 N hydrochloric acid, is added dropwise to the reaction mixture. The latter is agitated for 30 minutes at 0° and then allowed to warm up to room temperature. The solution is then concentrated under vacuum, 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 on 500 g of aluminum oxide, neutral, activity stage II, with hexane/ethyl acetate 3:2 as the eluting agent. Elution yields 3.39 g of 4,5-bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole, mp 179°-181°.

Workup

  1. temperaturethe solution is cooled to 0°
  2. concentrationThe solution is then concentrated under vacuum
  3. dry with materialthe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is chromatographed on 500 g of aluminum oxide
  6. washElution

Sources & evidence

ORD record
ord-fc15a55b6b824d86a2f2f4b12b1e1b64
Source dataset
uspto-grants-1983_09
Patent number
US04402960

Reaction notes

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