4-Bromophenacyl bromide → 4-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

HRID 52302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52302
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][CH:31]=1)=O>C(O)(C)C>[Br:36][C:33]1[CH:34]=[CH:35][C:30]([C:28]2[N:20]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=3)[CH:27]=2)=[CH:31][CH:32]=1

Komponenten

5

Edukt 3

HCID 74544-Bromophenacyl bromideHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Produkt 1

HCID 221490044-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazoleAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (400 mg, 1.29 mmol) and sodium bicarbonate (216 mg, 2.59 mmol) in isopropanol (30 mL), 2,4'-dibromoacetophenone (720 mg, 2.58 mmol) was added. After heating the reaction mixture at 80°-85° C. for 18 hours, the solvent was removed. The residue was redissolved in methylene chloride and washed with aqueous sodium bicarbonate and water. The organic fractions were combined, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product (810 mg) was chromatographed (silica gel, hexane/ethyl acetate, 6/4) to give 4-(4-bromophenyl)-2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazole (400 mg, 64%) as a pale yellow solid: mp 145°-48° C. Anal. Calc'd. for C22H16N2SO2BrCl: C, 54.17, H, 3.31, N, 5.74, S, 6.57. Found: C, 54.41, H, 3.33, N, 5.50, S, 6.52.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter heating the reaction mixture at 80°-85° C. for 18 hours
  3. customthe solvent was removed
  4. dissolutionThe residue was redissolved in methylene chloride
  5. washwashed with aqueous sodium bicarbonate and water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product (810 mg) was chromatographed (silica gel, hexane/ethyl acetate, 6/4)

Quellen und Nachweise

ORD-Eintrag
ord-fce1c3f8c37843a8b3883298659ddd39
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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