5-(4-BROMOPHENYL)-1,3,4-OXADIAZOL-2-AMINE synthesis

7synthesis methods

Product Name:5-(4-BROMOPHENYL)-1,3,4-OXADIAZOL-2-AMINE
CAS Number:33621-62-4
Molecular formula:C8H6BrN3O
Molecular Weight:240.06

506-68-3
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$10.00/1g

5798-75-4 Synthesis

5798-75-4
191 suppliers
$6.00/5g

5-(4-BROMOPHENYL)-1,3,4-OXADIAZOL-2-AMINE

33621-62-4
18 suppliers
$125.00/1g

Yield:33621-62-4 72%

Reaction Conditions:

Stage #1: Ethyl 4-bromobenzoatewith hydrazine hydrate in ethanol; for 16 h;Reflux;
Stage #2: bromocyane in ethanol; for 16 h;Reflux;

Steps:

5-(4-bromophenyl)-1,3,4-oxadiazol-2-amine (1)

To a stirred solution of ethyl 4-bromobenzoate I (50 g, 0.218 mol) in Ethanol (750 mL) was added hydrazine hydrate (50 mL, 1 vol) and stirred at reflux temp for 16 h. The solvent was evaporated, the residue was triturated with pet ether to give hydrazide. The hydrazide was taken in Ethanol (500 mL) and added cyanogen bromide (34 g, 0.327 mmol) and stirred at RT for 16 h. After completion, the solvent was evaporated and the residue was poured into ice water and filtered the solid to obtain oxadiazole 1 (37.7 g, 72%, over two steps) as a white solid; m. p. 270-272 °C; IR (KBr) υ: 3292, 3110, 1660 cm-1; 1H NMR (DMSO-d6, 300 MHz): δ 7.75 (t, 4H, Phenyl), 7.35 (s, 2H, -NH2) 13CNMR (DMSO-d6, 75 MHz): δ 163.7, 156.6, 132.3, 126.9, 123.7, 123.4; Lit-35 1H NMR (CDCl3): δ 7.25-7.69 (dd, 4H, J = 2.6, 5.6 Hz, Ar-H), 7.75 (s, 2H, NH); 13C NMR (CDCl3): 144-130 (Ar-C).LC-MS: m/z 240.09 (M+H). HRMS. Calcd. for C8H7BrN3O: 240.0875, Found: 240.0879.

References:

Devarasetty, Kiran;Tharikoppula, Giri;Sridhar, Tailor;Eppakayala, Laxminarayana;Kyasani, Mahesh;Arumugam, Premkumar;Pusuluri, Srinivas [Synthetic Communications,2016,vol. 46,# 3,p. 263 - 274] Location in patent:supporting information

506-68-3
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$10.00/1g

5933-32-4 Synthesis