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

HRID 1252494Notes

Reaction equation

HRID 1252494 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-74bd5679caa44f69999dd1169ecc5115
Source dataset
uspto-grants-1988_05
Patent number
US04743613

Reaction notes

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