Hydrochloric Acid → HCID 178504686, compound

HRID 1241792Notes

Reaction equation

HRID 1241792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([O:15]C)=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13](=[O:14])[C:12]([OH:15])=[C:11]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)[CH:10]=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 219340392-(3-chlorophenyl)-4-(methoxy)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone

Product 1

HCID 178504686HCID 178504686, compoundYield 112.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 2-(3-chlorophenyl)-4-(methoxy)-5-[4-(methylsulfonyl)phenyl]-3(2H)-pyridazinone (6.26 g, 16 mmol) in 5% NaOH (54 mL) dioxane (39.4 mL) was heated at reflux and stirred for 1.5 hours. As the reaction proceeds, the solution becomes orange and homogeneous. The mixture was cooled and poured into 1N HCl, with constant stirring. The resulting white solid was filtered and rinsed with H2O and left to dry overnight. The mostly dry product was taken up in CH2Cl2 and azeotroped with toluene to remove any remaining H2O, to provide the desired product as a white solid (yield: 6.79 g, >100%). 1H NMR (300 MHz, DMSO d6) δ 2.27 (s, 3H), 7.51–7.62 (m, 2H), 7.68 (m, 1H), 7.79 (m, 1H), 8.03 (m, 4H), 8.24 (s, 1H). MS (DCI/NH3) m/z 377 (M+H)+, 396 (M+NH4)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customAs the reaction proceeds
  4. temperatureThe mixture was cooled
  5. filtrationThe resulting white solid was filtered
  6. washrinsed with H2O
  7. waitleft
  8. customto dry overnight
  9. customazeotroped with toluene
  10. customto remove any remaining H2O

Sources & evidence

ORD record
ord-3959a14b405b4d0da690d38126a3d8df
Source dataset
uspto-grants-2006_10
Patent number
US07115591B2

Reaction notes

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