Selenium Dioxide → 6-Methoxy-1,3-benzothiazole-2-carbaldehyde

HRID 2050780Notes

Reaction equation

HRID 2050780 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH3:10])[S:9][C:5]=2[CH:4]=1.[Se](=O)=[O:14]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[N:7]=[C:8]([CH:10]=[O:14])[S:9][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 762546-Methoxy-2-methylbenzothiazole

Product 1

HCID 145989816-Methoxy-1,3-benzothiazole-2-carbaldehydeYield 55.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Oxidation of 6-methoxy-2-methylbenzothiazole (10.0 g, 55.9 mmole) with selenium dioxide (6.2 g, 55.9 mmole) in 300 ml dioxane for six hours by the method of Preparation H gave 6.0 g of 6-methoxy-2-formylbenzothiazole after chromatography of the crude product on silica gel, eluting with chloroform. 1H-NMR(CDCl3)-ppm(delta): 3.9 (s, 3H), 7.1-7.5 (m, 2H), 8.0-8.3(m, 1H), 10.1 (s, 1H).

Sources & evidence

ORD record
ord-2c5bac721512431480f0c45ebb6700b8
Source dataset
uspto-grants-1991_05
Patent number
US05015473

Reaction notes

Loading…