m-Chloroperbenzoic acid → HCID 58072456, compound

HRID 1624746Notes

Reaction equation

HRID 1624746 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[C:11]([C:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:19]=[CH:18][CH:17]=3)=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CSC1C=C(N2C=CC(=[O:41])C(C3C=CN(C4C=CC=CC=4)N=3)=N2)C=CC=1.C(=O)(O)[O-].[Na+].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[C:5]([N:9]2[CH:14]=[CH:13][C:12](=[O:15])[C:11]([C:16]3[N:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:19]=[CH:18][CH:17]=3)=[N:10]2)[CH:6]=[CH:7][CH:8]=1)=[O:41]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 59436285HCID 59436285, compoundHCID 66711296HCID 66711296, compound

Product 1

HCID 58072456HCID 58072456, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-[3-(methylsulfanyl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one and 1-[3-(methylsulfanyl)phenyl]-3-(1-phenyl-1H-pyrazol-3-yl)pyridazin-4(1H)-one (0.180 g, 0.50 mmol), sodium bicarbonate (0.168 g, 2.0 mmol) in methylene chloride (8 mL) was treated with 3-chloroperoxybenzoic acid (0.140 g, 77%, 0.62 mmol) and the resulting mixture was stirred at ambient temperature for 2 h. After this time, the reaction was diluted with methylene chloride (20 mL), quenched with sodium thiosulfate (10%, 30 mL) and extracted with methylene chloride (2×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography (silica, methylene chloride to 1:10 methanol/methylene chloride), followed by preparative HPLC gave 1-[3-(methylsulfinyl)phenyl]-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (84 mg, 45%) as a white solid.

Workup

  1. customquenched with sodium thiosulfate (10%, 30 mL)
  2. extractionextracted with methylene chloride (2×20 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a1e1167d680d42d4a73c1f6b54d2e064
Source dataset
uspto-grants-2014_07
Patent number
US08778944B2

Reaction notes

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