Sodium Bicarbonate → HCID 22997889, compound

HRID 1352950Notes

Reaction equation

HRID 1352950 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:42])[CH2:29][O:30][CH2:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=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:42])([CH2:29][O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)[N:20]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 22997979HCID 22997979, compoundHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 22997889HCID 22997889, compound

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-(2-quinolylmethoxy)-2-propanone from Step 1 (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-[(2-quinolylmethoxy)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-dc755b68fd7e4d2fa25fd62588714d0d
Source dataset
uspto-grants-2007_05
Patent number
US07220770B2

Reaction notes

Loading…