Sodium Bicarbonate → HCID 86750631, compound

HRID 52320Notes

Reaction equation

HRID 52320 reaction equation
ClC1C=CC([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)=CC=1.C(=O)(O)[O-].[Na+].Br[CH2:27][C:28](=O)COC>CC(C)=O>[CH3:19][S:16]([C:13]1[CH:12]=[CH:11][C:10]([N:9]2[CH2:28][CH2:27][N:20]=[CH:8]2)=[CH:15][CH:14]=1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 126260601-Bromo-3-methoxypropan-2-oneHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

Product 1

HCID 86750631HCID 86750631, 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-methoxy-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 chromatographed (silica gel, toluene/ethyl acetate) to give 2-(4-chlorophenyl)-4-hydroxy-4-[methoxy)methyl]-1-[4-(methylsulfonyl)phenyl]-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 chromatographed (silica gel, toluene/ethyl acetate)

Sources & evidence

ORD record
ord-541d57af5dad4dea8d1e445a20436294
Source dataset
uspto-grants-1997_04
Patent number
US05616601

Reaction notes

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