5-(2-FURYL)-1,3,4-THIADIAZOL-2-AMINE synthesis
- Product Name:5-(2-FURYL)-1,3,4-THIADIAZOL-2-AMINE
- CAS Number:4447-45-4
- Molecular formula:C6H5N3OS
- Molecular Weight:167.19
Yield:4447-45-4 97%
Reaction Conditions:
Stage #1: 2-Furoic acid;thiosemicarbazidewith trichlorophosphate at 75; for 0.5 h;
Stage #2: with water for 4 h;Reflux;
Steps:
21 5.1.1.21. 5-(Furan-2-yl)-1,3,4-thiadiazol-2-amine (80)
General procedure: 5.1.1
5-(4-Morpholinophenyl)-1,3,4-thiadiazol-2-amine (59)
A mixture of 4-morpholinobenzoic acid (5.18 g, 25 mmol) and N-aminothiourea (2.28 g, 25 mmol) in POCl3 (7 ml) was stirred vigorously at 75 °C for 0.5 h.
After addition of H2O (30 ml), the reaction mixture was heated under reflux for 4 h and basified to pH 8 by 50% NaOH solution.
The mixture was filtered and the filter cake was recrystallized from ethanol to yield 3.90 g of compound 59 as a yellow crystal. Yield: 59%; The synthetic procedures of compounds 60-81 were the same as that described above. 5.1.1.21
5-(Furan-2-yl)-1,3,4-thiadiazol-2-amine (80)
Yield: 97%, mp: 247-249 °C (EtOH). ESI-MS m/z: 168.3 [M+H]+; 1H NMR (DMSO-d6) δ 6.65-6.66 (m, 1H), 6.95 (d, J = 3.6 Hz, 1H), 7.45 (s, 2H), 7.83-7.84 (m, 1H).
References:
Guan, Peng;Wang, Lei;Hou, Xuben;Wan, Yichao;Xu, Wenfang;Tang, Weiping;Fang, Hao [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 21,p. 5766 - 5775]
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