2-(p-Chlorophenyl)-4H-3,1-benzoxazin-4-one synthesis

11synthesis methods

Product Name:2-(p-Chlorophenyl)-4H-3,1-benzoxazin-4-one
CAS Number:18600-52-7
Molecular formula:C14H8ClNO2
Molecular Weight:257.67

34425-87-1 Synthesis

34425-87-1
14 suppliers
inquiry

2-(p-Chlorophenyl)-4H-3,1-benzoxazin-4-one

18600-52-7
8 suppliers
$106.00/250mg

Yield:18600-52-7 95%

Reaction Conditions:

with acetic anhydrideReflux;

Steps:

4.1.8. Synthesis of 2-(4-chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 4b

A suspension of 2-(4-chlorobenzamido)benzoic acid 3b (2.5 g,1.0 equiv) was refluxed in Ac2O (15.0 equiv) and treated accordingly to general procedure b, previously reported, to obtain title compound 4b as a white solid. 2-(4-Chlorophenyl)-4H-benzo[d][1,3]oxazin-4-one 4b: yield 60%; silica gel TLC Rf= 0.80 (Ethyl acetate/n-hexane 50% v/v); mp189-190C;dH(400 MHz, DMSO-d6) 7.70 (3H, m), 7.77 (1H, d, J8.0), 8.00 (1H, t,J 8.0), 8.20 (1H, d,J 8.0), 8.23 (2H, d,J 8.8);dC(100 MHz, DMSO-d6) 117.6, 127.7, 128.8, 129.5, 129.7, 129.9,130.3, 137.6, 138.4, 146.9, 156.4, 159.3. Experimental in agreement with reported data.

References:

Bozdag, Murat;Alafeefy, Ahmed M.;Vullo, Daniela;Carta, Fabrizio;Dedeoglu, Nurcan;Al-Tamimi, Abdul-Malek S.;Al-Jaber, Nabila A.;Scozzafava, Andrea;Supuran, Claudiu T. [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 24,p. 7751 - 7764]