Imidazole → 1-(1-Imidazolyl)-3-phenylsulfonylpropan-2-one

HRID 746000Notes

Reaction equation

HRID 746000 reaction equation
Br[CH2:2][C:3](=[O:14])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].[NH:15]1[CH:19]=[CH:18][N:17]=[CH:16]1>C(Cl)Cl>[N:15]1([CH2:2][C:3](=[O:14])[CH2:4][S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 122775531-(Benzenesulfonyl)-3-bromopropan-2-one

Product 1

HCID 136889551-(1-Imidazolyl)-3-phenylsulfonylpropan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 50 g (0.180 mole) finely ground 1-bromo-3-phenylsulfonylpropan-2-one (the product of Example 10) in 125 ml methylene chloride cooled to about 0°-5° C., 36.8 g (0.54 mole) imidazole in 300 ml methylene chloride were added dropwise. The reaction mixture was maintained at 0°-5° C. for one hour, allowed to warm to room temperature and was stirred overnight. The methylene chloride was removed in vacuo at room temperature. The resulting oil was partitioned with 200 ml water and 200 ml ethyl acetate. The aqueous phase was extracted with ethyl acetate (four times 125 ml). The combined ethyl acetate extracts were treated with decolorizing charcoal, dried, filtered and concentrated. The precipitate which formed was triturated with methanol-isopropyl alcohol yielding 17.9 g of the above-identified product, as an off-white solid, melting point 137°-140° C.

Workup

  1. temperaturecooled to about 0°-5° C.
  2. temperatureThe reaction mixture was maintained at 0°-5° C. for one hour
  3. customThe methylene chloride was removed in vacuo at room temperature
  4. customThe resulting oil was partitioned with 200 ml water and 200 ml ethyl acetate
  5. extractionThe aqueous phase was extracted with ethyl acetate (four times 125 ml)
  6. additionThe combined ethyl acetate extracts were treated with decolorizing charcoal
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe precipitate which formed
  11. customwas triturated with methanol-isopropyl alcohol yielding 17.9 g of the above-identified product, as an off-white solid, melting point 137°-140° C.

Sources & evidence

ORD record
ord-0df7efa495e946d19cbb476e1b526f2b
Source dataset
uspto-grants-1986_07
Patent number
US04602030

Reaction notes

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