Toluene → N-[5-(1,2-Dithiolan-3-yl)pentyl]acetamide

1 ml of butylamine was added to a mixture of 1.3 mmol of 2-[5-(1,2-dithiolan-3-yl)pentyl]isoindole-1,3-dione, 9 ml of toluene and 2 ml of methanol. The resulting mixture was stirred at room temperature for 3 hours, after which the reaction mixture was allowed to stand at room temperature for 2 days. 1 ml of butylamine was then added to the reaction mixture. The resulting mixture was stirred at room temperature for 3 hours. The solvent was then removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. 5 ml of anhydrous tetrahydrofuran were then added to the residue. 0.28 ml of triethylamine and 0.14 ml of acetyl chloride were then added to dropwise to the resulting mixture, whilst ice-cooling, and then the mixture was stirred at room temperature for 1 hour and 30 minutes. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. The residue was subjected to silica gel column chromotagraphy, using 1:0 and 10:1 by volume mixtures of ethyl acetate and methanol as eluent. The solvent was removed from the eluate by distillation under reduced pressure. The residue was dissolved in dioxane, after which it was lyophilised, to give 161 mg of the title compound as yellow crystals, melting at 28 to 33° C.

1. waitto stand at room temperature for 2 days
2. stirringThe resulting mixture was stirred at room temperature for 3 hours
3. customThe solvent was then removed from the reaction mixture by distillation under reduced pressure
4. additionWater was added to the residue
5. extractionafter which it was extracted with ethyl acetate
6. washThe extract was washed with a saturated aqueous solution of sodium chloride
7. dry with materialdried over anhydrous sodium sulfate
8. customEthyl acetate was removed from the
9. extractionextract by distillation under reduced pressure
10. addition5 ml of anhydrous tetrahydrofuran were then added to the residue
11. addition0.28 ml of triethylamine and 0.14 ml of acetyl chloride were then added to dropwise to the resulting mixture, whilst ice-
12. temperaturecooling
13. stirringthe mixture was stirred at room temperature for 1 hour and 30 minutes
14. customAt the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure
15. additionWater was added to the residue
16. extractionafter which it was extracted with ethyl acetate
17. washThe extract was washed with a saturated aqueous solution of sodium chloride
18. dry with materialdried over anhydrous sodium sulfate
19. customEthyl acetate was removed from the
20. extractionextract by distillation under reduced pressure
21. customThe solvent was removed from the
22. distillationeluate by distillation under reduced pressure
23. dissolutionThe residue was dissolved in dioxane

ORD record

ord-7e94d3f2a3714192a21c7d0e5726f449

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06013663