Application of 17564-64-6, 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. 17564-64-6 name is 2-(Chloromethyl)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.
General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.63 2-((2-(2-(2-Methylcyclopentylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (11C) White powder, mp 158-162 C, 83% yield; 1H NMR (400 MHz, CDCl3): delta 1.14-1.17 (d, J = 10 Hz, 3H, CH3), 1.28-1.31 (m, 2H, cyclopentane), 1.83 (bs, 1H, cyclopentane), 1.98-2.02 (m, 1H, cyclopentane), 2.25-2.30 (m, 1H, cyclopentane), 2.48-2.54 (m, 2H, cyclopentane), 3.83 (s, 2H, CH2, thiazolidinone), 5.71 (s, 2H, ArCH2), 7.76-7.77 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar). 13C NMR (100 MHz, CDCl3): delta 16.9, 22.5, 30.3, 32.5, 33.7, 39.6, 45.1, 123.6, 131.7, 134.3, 157.9, 166.7, 171.0, 182.3.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Chloromethyl)isoindoline-1,3-dione, and friends who are interested can also refer to it.
Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem