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

HRID 370766Notes

Reaction equation

HRID 370766 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([S:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:25]=3N)[NH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.O1CCOCC1.Cl.N(OCCC(C)C)=O>C(O)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([S:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=3)[NH:13][C:14]=2[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 312751,4-DioxaneHCID 202754084,5-Bis(4-methoxyphenyl)-2-(2-amino-4-trifluoromethylphenylthio)imidazole hydrochloride

Product 1

HCID 128323054,5-Bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazoleYield 85.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.61 g of 4,5-bis(4-methoxyphenyl)-2-(2-amino-4-trifluoromethylphenylthio)imidazole hydrochloride is suspended in a mixture of 70 ml of absolute ethanol, 30 ml of absolute dioxane, and 365 mg of hydrochloric acid and combined at 0° with 0.586 g of isoamyl nitrite. The mixture is agitated for 30 minutes, then heated for 2 hours to boiling, and the solution evaporated to dryness under vacuum. The residue is distributed between ethyl acetate and sodium bicarbonate solution. The organic solution is dried over sodium sulfate and concentrated to dryness under vacuum. The residue is crystallized from ether/methylene chloride, thus obtaining 2.01 g of 4,5-bis(4-methoxyphenyl)-2-(4-trifluoromethylphenylthio)imidazole, mp 184°-186°.

Workup

  1. temperatureheated for 2 hours
  2. customthe solution evaporated to dryness under vacuum
  3. dry with materialThe organic solution is dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is crystallized from ether/methylene chloride

Sources & evidence

ORD record
ord-0262edc729b24efca187fc629eccbf70
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

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