Hexachloroethane → 1-chloro-10H-phenothiazine

This compound was prepared according to a procedure by A. R. Katritzky et al., Synthesis, 1988, 215-217. To a solution of phenothiazine (10.0 g, 50.18 mmol) in anhydrous THF (200 mL) and cooled to −78° C. was added a solution of n-BuLi (24.1 mL, 60.2 mmol, 2.5 M in hexanes) dropwise. The mixture was stirred until a yellow precipitate formed, and then allowed to warm to room temperature, until a clear yellow solution resulted. The solution was again cooled to −78° C. and CO2 gas was bubbled through the mixture for 5 min. The resulting solution was allowed to warm to RT and the solvent was evaporated to give a residue. The residue was again dissolved in anhydrous THF (200 mL) and cooled to −78° C., before t-BuLi (50 mL, 85 mmol, 1.7 M in pentane) was added dropwise. The resulting mixture was allowed to warm to −20° C. and was stirred at this temperature for 2 h. The reaction mixture was again cooled to −78° C. and a solution of hexachloroethane (100 mmol) in THF (50 mL) was added dropwise. The mixture was stirred at this temperature for 1 hour then allowed to warm to −20° C. and stirred for 2 h. The reaction mixture was quenched with ice cold 1 N HCL and extracted with EtOAC. The combined organic layers were washed with brine, dried over MgSO4, filtered and evaporated to give a residue. The residue was purified by flash silica gel chromatography to give of an beige solid.

1. customThis compound was prepared
2. customKatritzky et al., Synthesis, 1988, 215-217
3. customformed
4. customresulted
5. temperatureThe solution was again cooled to −78° C.
6. customCO2 gas was bubbled through the mixture for 5 min
7. temperatureto warm to RT
8. customthe solvent was evaporated
9. customto give a residue
10. additionwas added dropwise
11. temperatureto warm to −20° C.
12. stirringwas stirred at this temperature for 2 h
13. temperatureThe reaction mixture was again cooled to −78° C.
14. stirringThe mixture was stirred at this temperature for 1 hour
15. temperatureto warm to −20° C.
16. stirringstirred for 2 h
17. customThe reaction mixture was quenched with ice cold 1 N HCL
18. extractionextracted with EtOAC
19. washThe combined organic layers were washed with brine
20. dry with materialdried over MgSO4
21. filtrationfiltered
22. customevaporated
23. customto give a residue
24. customThe residue was purified by flash silica gel chromatography
25. customto give of an beige solid

ORD record

ord-fbfc848c7cf443c5b9c0cb8c5a6be8bb

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785434B2