Water → HCID 21846927, compound

HRID 619734Notes

Reaction equation

HRID 619734 reaction equation
[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([N+:23]([O-:25])=[O:24])[C:10]([S:12][C:13]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][N:17]=[CH:18]4)=[CH:11][C:6]=2[N:5]=[C:4]1[CH3:26])[CH3:2].[OH2:27].[OH-:28].[Na+]>S(=O)(=O)(O)O>[CH2:1]([N:3]1[C:7]2[CH:8]=[C:9]([N+:23]([O-:25])=[O:24])[C:10]([S:12]([C:13]3[CH:22]=[CH:21][CH:20]=[C:19]4[C:14]=3[CH:15]=[CH:16][N:17]=[CH:18]4)(=[O:28])=[O:27])=[CH:11][C:6]=2[N:5]=[C:4]1[CH3:26])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21846932HCID 21846932, compound

Product 1

HCID 21846927HCID 21846927, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

1-Ethyl-5-(5-isoquinolylsulfanyl)-2-methyl-6-nitro-1H-benzo[d]imidazole 300 mg (0.8 mmol) was dissolved in concentrated sulfuric acid 3 ml, Beckmann's reagent (K2Cr2O7 1 g, H2SO4 1 ml, H2O 9 ml) 6 ml was added dropwise, and the mixture was stirred overnight at room temperature. The reaction mixture was neutralized with 4N sodium hydroxide and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and 1-ethyl-5-(5-isoquinolylsulfonyl)-2-methyl-6-nitro-1H-benzo[d]imidazole 70 mg (20.8%) was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b22ad47cc08f427783d0e6dda61c49ca
Source dataset
uspto-grants-1999_09
Patent number
US05959107

Reaction notes

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