Dimethyl Sulfide → 6-(6-Bromo-5-nitroso-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2h)-pyridazinone

HRID 915051Notes

Reaction equation

HRID 915051 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[CH:21][C:22](=[O:28])[N:23]([CH:25]([CH3:27])[CH3:26])[N:24]=2)[C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:15][C:14]=1[N:35]=S(C)C.CSC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:12][C:13]1[N:18]=[C:17]([C:19]2[CH:20]=[CH:21][C:22](=[O:28])[N:23]([CH:25]([CH3:27])[CH3:26])[N:24]=2)[C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[N:15][C:14]=1[N:35]=[O:9]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 877986596-{6-bromo-5-[(dimethyl-lambda~4~-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3 (2H)-pyridazinone

Product 1

HCID 877873306-(6-Bromo-5-nitroso-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2h)-pyridazinoneYield 49.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of m-chloroperbenzoic acid (70-75% purity) (1.66 g) in CH2Cl2 (40 ml) was added a solution of 6-{6-bromo-5-[(dimethyl-lambda˜4˜-sulfanylidene)amino]-3-phenyl-2-pyrazinyl}-2-isopropyl-3 (2H)-pyridazinone (2.01 g) in CH2Cl2 (20 ml) at −10˜-5° C. and the mixture was stirred at the same temperature for one hour. After addition of dimethyl sulfide (0.25 ml), the solution was stirred at the same temperature for 30 minutes. Sat. aq. Na2CO3 (50 ml) was then added to the mixture. An organic layer was collected, dried over MgSO4, concentrated under reduced pressure and purified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v) to give 6-(6-bromo-5-nitroso-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone as a solid (0.896 g).

Workup

  1. stirringthe solution was stirred at the same temperature for 30 minutes
  2. customAn organic layer was collected
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. custompurified by column chromatography on silica gel eluting with a mixture of n-hexane and EtOAc (70:30 v/v)

Sources & evidence

ORD record
ord-d1997d09c60b4596949a9a39b9828b96
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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