Methanol → 1-(4'-Hydroxy-3'5'-difluorobenzyl)-2-(methylthio)imidazole

HRID 1252494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252494
C[O:2][C:3]1[C:15]([F:16])=[CH:14][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][NH:10][C:9]2=[S:13])=[CH:5][C:4]=1[F:17].B(Br)(Br)Br.[CH3:22]O>C(Cl)Cl>[OH:2][C:3]1[C:15]([F:16])=[CH:14][C:6]([CH2:7][N:8]2[CH:12]=[CH:11][N:10]=[C:9]2[S:13][CH3:22])=[CH:5][C:4]=1[F:17]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 25134Boron tribromideHCID 144508631-[(3,5-Difluoro-4-methoxyphenyl)methyl]-1,3-dihydro-2H-imidazole-2-thione

Produkt 1

HCID 201401331-(4'-Hydroxy-3'5'-difluorobenzyl)-2-(methylthio)imidazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 1-(4'-methoxy-3',5'-difluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione (0.0046 mol) in 40 ml methylene chloride is treated with a solution of BBr3 (0.014 mol) in 10 ml methylene chloride. After four hours methanol is cautiously added, the mixture is stirred for an additional eighteen hours and the solvents are evaporated. The residue is dissolved in water, washed with ethyl acetate, neutralized with sodium bicarbonate, and extracted with ethyl acetate. The extracts are dried (MgSO4) and filtered and the solvent evaporated to yield 1-(4'-hydroxy-3'5'-difluorobenzyl)-2-(methylthio)imidazole. This compound then is substituted for 1-(4'-hydroxy-3',5'-difluorobenzyl)-1,3-dihydro-2H-imidazole-2-thione in the process of Example 1 to yield 1-(4'-acetoxy-3',5'-difluorobenzyl)-2-(methylthio)imidazole.

Aufarbeitung

  1. customthe solvents are evaporated
  2. dissolutionThe residue is dissolved in water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extracts are dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-74bd5679caa44f69999dd1169ecc5115
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743613

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