Thionyl Chloride → 1H-indole-2-carbonyl Chloride

According to the synthesis scheme shown above, a mixture of indole-2-carboxylic acid (98 mg, 0.61 mmol, purchased from ACROS Co.), 10 ml benzene and thionyl chloride (SOCl2) (224 ml, 3.1 mmol) was placed in a 50 ml round-bottom flask purged with nitrogen gas and refluxed for 2 h while stirring, followed by cooling to room temperature. The mixture was concentrated to dry within a concentrator under a reduced pressure, and after the addition of 10 ml benzene, the mixture was concentrated again. Excess thionyl chloride (SOCl2) was removed from the mixture by three repeats of adding 10 ml benzene and concentrating the mixture, thus obtaining the title compound in the form of a yellow solid.

1. customAccording to the synthesis scheme
2. customwas placed in a 50 ml round-bottom flask
3. custompurged with nitrogen gas
4. temperaturerefluxed for 2 h
5. concentrationThe mixture was concentrated
6. customto dry within a concentrator under a reduced pressure
7. additionafter the addition of 10 ml benzene
8. concentrationthe mixture was concentrated again
9. customExcess thionyl chloride (SOCl2) was removed from the mixture by three repeats
10. additionof adding 10 ml benzene
11. concentrationconcentrating the mixture

ORD record

ord-9177136f040a4304973b27ebd5bd3a61

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06939869B2