Synthetic Route of 5181-35-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 5181-35-1 name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
To a solution of 2-(2-bromoethoxy) isoindoline-l,3-dione (10 g, 37 mmol) and tert-buty 2-(lH-tetrazol-5-yl)ethylcarbamate (7.88 g, 37 mmol) in dimethyl formamide (50 ml) was added cesium carbonate ((14.48 g, 44 mmole) in portion wise at 25-30 C under stirring. The reaction mixture was stirred for further 16 hours and filtered; the filtrate was slowly poured into chilled water (400 ml) under stirring and continued stirring for 30 minutes. The formed precipitates of compound were filtered and washed with water (40 ml). The solid compound was dried at 40C for 2 hour under high vacuum, yielded 12 g. The compound was column purified using hexane and acetone as an eluent. The mixture was isolated at 10-15% concentration of acetone in hexane to yield 10 g of 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione in 67% yield Analysis: Mass: 403 (M+l); for Molecular weight: 402 and Molecular formula: C18H22N6O5..; Hydrazine hydrate monohydrate (1.86 ml, 037.3 mmol) was added to a solution of 2-{2-[5-(2- tertiary-butoxy-carbonyl-aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2- {2-[5-(2-tertiary-butoxy-carbonyl-aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)- dione (10 g, 24.8 mmol, obtained from step 1) in dichloromethane (10 ml) under stirring at room temperature. After completion of 2 hours of stirring at same temperature the TLC confirms the completion of reaction. The reaction mass was filtered and the solid was washed with dichloromethane (50 ml). The collected filtrate was concentrated at 40C under vacuum to yield 6.75 g of the product, which was used further without any purification. Analysis: Mass: 273 (M+l); for Molecular weight: 272 and Molecular formula: CioH2oN603.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Bromoethoxy)isoindoline-1,3-dione, and friends who are interested can also refer to it.
Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem