Sodium periodate → (5-Chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetaldehyde

5-chloro-3-(2-propen-1-yl)-1,3-benzothiazol-2(3H)-one (0.43 g, 1.9 mmol) (0.43 g, 1.9 mmole) was dissolved in 1,4-dioxane (20 ml) and water (22 ml) was added. Sodium periodate (0.94 g, 4.4 mmol) was added followed by 4% osmium tetroxide in water (2.1 ml) and stirred at rt for 30 mins after which time a heavy precipitate had formed. Water (20 ml) was added followed by more sodium periodate (1.9 g, 8.9 mmol) and the mixture stirred at rt for 18 h. The mixture was concentrated in-vacuo to a small volume and partitioned between water (50 ml) and DCM (2×50 ml). The organics were separated and dried. Chromatography on silica gel eluting with a gradient of 25-100% ethyl acetate/40-60 petroleum ether gave 0.21 g, 48%) of the title compound.

1. customhad formed
2. stirringthe mixture stirred at rt for 18 h
3. concentrationThe mixture was concentrated in-vacuo to a small volume
4. custompartitioned between water (50 ml) and DCM (2×50 ml)
5. customThe organics were separated
6. customdried

ORD record

ord-895574a5566d4f2d91bd0ae64cb33c60

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071592B2