Triphenylphosphine → 1-Methyl-5-(benzoylthiomethyl)imidazole

HRID 992695Notes

Reaction equation

HRID 992695 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7]O)=[CH:5][N:4]=[CH:3]1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]([OH:48])(=[S:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH3:1][N:2]1[C:6]([CH2:7][S:47][C:40](=[O:48])[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:5][N:4]=[CH:3]1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 2773450(1-methyl-1H-imidazol-5-yl)methanolHCID 5462977Diethyl azodicarboxylateHCID 178526132HCID 178526132, compound

Product 1

HCID 184116101-Methyl-5-(benzoylthiomethyl)imidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere, 1-methyl-5-hydroxymethylimidazole (2.52 g), diethylazodicarboxylate (4.26 ml) was added successively to a solution of triphenylphosphine (7.07 g) in THFe (50 ml) with ice cooling, while the reaction temperature was kept below 15 degree. After stirring for 1 hour at 0° C., 3.9 ml of thiobenzoic acid was added slowly. The mixture was poured into a mixture of ethyl acetate and aqueous sodium hydrogen carbonate. The aqueous layer was separated, the organic layer was washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on silica gel (eluent: dichloromethane-acetone) to afford 1-methyl-5-(benzoylthiomethyl)imidazole (993 mg).

Workup

  1. customwas kept below 15 degree
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified on silica gel (eluent: dichloromethane-acetone)

Sources & evidence

ORD record
ord-991fdb0210794e938b472c1dfab2d7ca
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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