5-(4-BROMOPHENYL)-1,3,4-OXADIAZOL-2-AMINE synthesis
- 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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5798-75-4
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33621-62-4
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$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
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$8.00/1g
33621-62-4
20 suppliers
$125.00/1g
1122-91-4
703 suppliers
$9.00/10g
33621-62-4
20 suppliers
$125.00/1g
563-41-7
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$5.00/25g
1122-91-4
703 suppliers
$9.00/10g
33621-62-4
20 suppliers
$125.00/1g
99-90-1
484 suppliers
$6.00/25g
33621-62-4
20 suppliers
$125.00/1g