Sodium Bicarbonate → 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl) phenyl]-4-[(phenylthio)methyl]-4,5-dihydro-1H-imidazole

HRID 1352948Notes

Reaction equation

HRID 1352948 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](=[O:37])[CH2:29][S:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[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)[CH2:27][C:28]([OH:37])([CH2:29][S:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 229980621-Bromo-3-phenylthio-2-propanoneHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 229979662-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl) phenyl]-4-[(phenylthio)methyl]-4,5-dihydro-1H-imidazole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 4-chloro-N-(4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (1 mmol) and sodium bicarbonate (2 mmol) in acetone (20 mL), 1-bromo-3-phenylthio-2-propanone (1.5 mmol) is added. After heating to reflux for 24 hours, the reaction mixture is filtered, washed with acetone and concentrated in vacuo. The crude product is purified by chromatography (silica gel, toluene/ethyl acetate) to give 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl) phenyl]-4-[(phenylthio)methyl]-4,5-dihydro-1H-imidazole.

Workup

  1. additionis added
  2. temperatureAfter heating
  3. temperatureto reflux for 24 hours
  4. filtrationthe reaction mixture is filtered
  5. washwashed with acetone
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by chromatography (silica gel, toluene/ethyl acetate)

Sources & evidence

ORD record
ord-52b7933ae91d4a32b1a2e5b9353bb3a9
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

Loading…