Chemical Properties
Crystallized (ethanol). Melting point 115-117°C.
Uses
5-Chloro-3-phenyl-2,1-benzisoxazole, is a Heterocyclic Building Block used for the synthesis of pharmaceuticals and other organic compounds. It is used in the synthesis of novel 2H-1, 4-benzodiazepine-2-ones as inhibitors of HIV-1 transcription.It can also be sued for the synthesis of Nitroacridinones derivatives.
Synthesis
General procedure for the synthesis of 5-chloro-3-phenylbenzo[c]isoxazoles from 2-amino-5-chlorobenzophenone: Oxone (0.270 g, 0.44 mmol) was added to (E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (1 g, 0.44 mmol) in a MeCN/H?O (2.5 mL/2.5 mL) solution. The reaction mixture was stirred at room temperature and the reaction progress was monitored by TLC and GC-MS. After stirring for 24 h, H?O (150 mL) and CH?Cl? (150 mL) were added for extraction. The organic layer was separated and the aqueous layer was further extracted with CH?Cl? The combined organic layers were washed with H?O, dried over anhydrous Na?SO?, filtered and concentrated. Purification by silica gel column chromatography (n-hexane/EtOAc, 98:2) afforded 3 g of the target product 2,1-benzisoxazole.
References
[1] Synthesis (Germany), 2016, vol. 48, # 18, p. 3017 - 3030
[2] Helvetica Chimica Acta, 1979, vol. 62, p. 185 - 197
