Iodoethane → 10H-Phenothiazine, 1-ethyl-

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 is stirred until a yellow precipitate forms and then allowed to warm to room temperature, until a clear yellow solution results. the solution is again cooled to −78° C. and CO2 gas is bubbled through the mixture for 5 min. The resulting solution is 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 ethyl iodide (100.0 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 1N 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 the desired product.

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

ORD-Eintrag

ord-18746ab1a03b4a6da98841e99394f049

Quelldatensatz

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08785434B2