(1,3-Benzothiazol-2-yl)methanol → 1,3-Benzothiazole-2-carbaldehyde

5.47 g of manganese dioxide were added at room temperature to a solution of 2.26 g of 2-hydroxymethylbenzothiazole in 20 ml of acetone. The resulting mixture was stirred under reflux for 5 hours, at the end of which time the temperature of the mixture was cooled to room temperature and the mixture was left to stand for 14 hours. A further 3.06 g of manganese dioxide were then added and the resulting mixture was stirred under reflux for 6 hours. At the end of this time, the reaction mixture was cooled to room temperature and then filtered. The resulting filtrate was concentrated by evaporation under reduced pressure, petroleum ether was added to the thus obtained crude crystalline solid and the mixture was filtered. The filtrate was then concentrated to about half its volume causing precipitation of a crystalline solid which was filtered off and dried in vacuo to give 432.6 mg (yield 19.3%) of the title compound as a solid having a melting point of 69° to 70° C.

1. temperatureunder reflux for 5 hours, at the end of which time the temperature of the mixture
2. waitthe mixture was left
3. stirringthe resulting mixture was stirred
4. temperatureunder reflux for 6 hours
5. temperatureAt the end of this time, the reaction mixture was cooled to room temperature
6. filtrationfiltered
7. concentrationThe resulting filtrate was concentrated by evaporation under reduced pressure, petroleum ether
8. additionwas added to the
9. customthus obtained crude crystalline solid
10. filtrationthe mixture was filtered
11. concentrationThe filtrate was then concentrated to about half its volume
12. customprecipitation of a crystalline solid which
13. filtrationwas filtered off
14. customdried in vacuo

ORD record

ord-eeedb14933554bee9ba0caab52f1a88e

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736487