Hydrogen Peroxide → 5,5-Dioxo-2-(6-methylpyridazin-3-ylamino)dibenzothiophene

HRID 2055320Notes

Reaction equation

HRID 2055320 reaction equation
OO.[CH3:3][C:4]1[N:9]=[N:8][C:7]([NH:10][C:11]2[CH:23]=[CH:22][C:14]3S[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[C:13]=3[CH:12]=2)=[CH:6][CH:5]=1.[S:24](=[O:28])(=O)(O)[OH:25]>C(O)(=O)C.C(Cl)Cl.CO>[O:25]=[S:24]1(=[O:28])[C:18]2[CH:19]=[CH:20][CH:21]=[CH:16][C:17]=2[C:13]2[CH:12]=[C:11]([NH:10][C:7]3[N:8]=[N:9][C:4]([CH3:3])=[CH:5][CH:6]=3)[CH:23]=[CH:22][C:14]1=2

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 222777962-(6-Methylpyridazin-3-ylamino)dibenzothiophene

Product 1

HCID 222778115,5-Dioxo-2-(6-methylpyridazin-3-ylamino)dibenzothiophene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Hydrogen peroxide (100 vols, 1 ml) was added to 2-(6-methylpyridazin-3-ylamino)dibenzothiophene Example 74; 300 mgs, 1.03 mmol) in acetic acid (3 ml) and conc. sulphuric acid (0.1 ml) and the mixture was heated to 60° C. for 40 minutes. On cooling to room temperature the mixture was diluted with DCM:MeOH (1:19) washed with aqueous potassium carbonate, dried over sodium sulphate and concentrated. Chromatography (eluent gradient of DCM to DCM:MeOH (1:1)) gave the product as an off white solid (0.131 g). NMR: 9.87 (brs, 1H), 8.48 (brs, 1H), 8.00-7.70 (m, 5H), 7.65 (t, 1H), 7.45 (d, 1H), 7.20 (d, 1H), 2.52 (s, 3H); m/z 324.28.

Workup

  1. washwashed with aqueous potassium carbonate
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f1ab4b3a14874053809c80fd81feb8e1
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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