Simple exploration of N-(6-Bromohexyl)phthalimide

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Related Products of 24566-79-8, A common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

11.9 g tritylsulfide 32 (43.1 mmol, 1.02 eq) were dissolved in 50 mL DMSO. 7.30 mL DBU (48.8 mmol; 1.14 eq) and 13.3 g phthalimide 31 followed by 15 mL DMSO were added. The mixture was stirred for 12 min at ambient temperature. 700 mL ethyl acetate and 200 mL 0.1 N HCl were added. The mixture was stirred until both solvent layers were clear. The layers were separated. The aqueous phase was extracted with ethyl acetate (3x, 50 mL each). The organic solutions were combined, washed with 80 mL sat. NaHC03and 80 mL brine, dried over Na2S04and filtered. The solvent was removed in vacuo. The residue was recrystallized from 240 mL ethanol under heating. The suspension was stored for 1 h at -18C. The trityl protected product 33 was filtered off, washed 2x with ethanol and dried under high vacuum. Yield: 19.6 g; 90 %MS: m/z = 528.07 [M+Na]+

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ASCENDIS PHARMA A/S; BISEK, Nicola; RAU, Harald; CLEEMANN, Felix; KNAPPE, Thomas; REIMANN, Romy; (140 pag.)WO2016/20373; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem