2-Bromo-2'-acetonaphthone → 2-(4-chlorophenyl)-1-(4-(methylsulfonyl)phenyl]-4-(2-naphthyl)-1H-imidazole

HRID 1166318Notes

Reaction equation

HRID 1166318 reaction equation
[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:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1)=O>C(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[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]=[C:28]([C:30]3[CH:39]=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=3)[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 691792-Bromo-2'-acetonaphthoneHCID 516892Sodium BicarbonateHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 221489462-(4-chlorophenyl)-1-(4-(methylsulfonyl)phenyl]-4-(2-naphthyl)-1H-imidazoleYield 54%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
82.5 °C

Procedure

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-bromo-2′-acetonaphthone (970 mg, 3.89 mmol) was added. After heating the reaction mixture at 80-85° C. for 20 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 (1.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-4-(2-naphthyl)-1H-imidazole (318 mg, 54%) as a pale yellow solid: mp 204-206° C. Anal Calc'd. for C26H19N2SO2Cl: C, 68.04, H, 4.17, N, 6.10, S, 6.99. Found: C, 67.65, H, 4.19, N, 5.96, S, 7.10.

Workup

  1. additionwas added
  2. customthe solvent was removed
  3. dissolutionThe residue was redissolved in methylene chloride
  4. washwashed with aqueous sodium bicarbonate and water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product (1.2 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-c00c7e177413462abdec0f45fb343677
Source dataset
uspto-grants-2003_09
Patent number
US06613789B2

Reaction notes

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