Selenium Dioxide → 5-Methoxy-4-nitro-2-benzothiazolecarboxaldehyde

HRID 1713720Notes

Reaction equation

HRID 1713720 reaction equation
[Se](=O)=[O:2].[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[C:15]=1[N+:16]([O-:18])=[O:17]>O1CCOCC1>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH:14]=[O:2])=[N:11][C:10]=2[C:15]=1[N+:16]([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 45077105HCID 45077105, compound

Product 1

HCID 241787235-Methoxy-4-nitro-2-benzothiazolecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

12.8 g (0.115 mol; 6 equivalents) of selenium dioxide is added to 4.34 g (19.3 mmol) of 5-methoxy-2-methyl-4-nitro-1,3-benzothiazole in solution in 180 ml of anhydrous dioxane. The reaction mixture is stirred at 80° C. for 18 hours then the insoluble matter is filtered and the solvent is evaporated off under reduced pressure. The expected aldehyde is obtained in the form of a yellow oil and purified on a silica column (eluent:ethyl acetate/heptane:gradient of 30% to 70%). Melting point: 154-155° C.

Workup

  1. filtrationthe insoluble matter is filtered
  2. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-952be467599143f58c30e65931d9dcd1
Source dataset
uspto-grants-2010_09
Patent number
US07795284B2

Reaction notes

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