2-Benzyl-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone → 2-Benzyl-4(4-fluorophenyl)-5-[4-(methylsulfinyl)phenyl]-3(2h)-pyridazinone

HRID 381872Notes

Reaction equation

HRID 381872 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][CH:23]=2)[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:30]C1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1>C(Cl)Cl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:11]([C:22]2[CH:23]=[CH:24][C:25]([S:28]([CH3:29])=[O:30])=[CH:26][CH:27]=2)[CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 101792462-Benzyl-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinoneHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 102237702-Benzyl-4(4-fluorophenyl)-5-[4-(methylsulfinyl)phenyl]-3(2h)-pyridazinoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2benzyl-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-3(2H)-pyridazinone, prepared according to the method of Example 4, (450 mg, 1.12 mmol) in CH2Cl2 (10 mL) was added dropwise to a suspension of hydroxy(tosyloxy)iodobenzene (439 mg, 1.12 mmol) in CH2Cl2 (15 mL) and the mixture was stirred until a clear solution was obtained (about 1 hour). The reaction mixture was then washed with water and dried with MgSO4. Removal of solvent in vacuo provided the corresponding sulfoxide (yield: 485 mg, about 100%). 1H NMR (300 MHz, CDCl3) δ 2.72 (s, 3H), 5.40 (s, 2H), 6.90 (m, 2H), 7.15 (m, 3H), 7.33 (m, 3H), 7.57 (m, 3H), 7.71 (m, 1H), 7.86 (s, 1H). MS m/z 419 (M+H)+, 436 (M+NH4)+.

Workup

  1. customwas obtained (about 1 hour)
  2. washThe reaction mixture was then washed with water
  3. dry with materialdried with MgSO4
  4. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-edb72116b98448b598929ad73dde5ec7
Source dataset
uspto-grants-2001_10
Patent number
US06307047B1

Reaction notes

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