5-pyrazinyl-1,3,4-oxadiazole-2-thione synthesis
- Product Name:5-pyrazinyl-1,3,4-oxadiazole-2-thione
- CAS Number:37545-39-4
- Molecular formula:C6H4N4OS
- Molecular Weight:180.19
Yield:37545-39-4 87%
Reaction Conditions:
with potassium hydroxide in ethanol; for 12 h;Reflux;
Steps:
5-(Pyrazin-2-yl)-1,3,4-oxadiazole-2-thiol(7a)
In a dried RB flask, KOH (1.42 g, 25.33 mmol) was suspended in ethanol (50 mL) atambient temperature. Then pyrazine-2-carbohydrazide6a (5 g, 36.19 mmol) was added and reaction mass was cooled.Carbon disulfide (2.4 mL, 39.81 mmol)was added dropwise and the resulting mixture was refluxed for 12 h. Thereaction progress was monitored by TLC and after completion of the reactionsolvent was distilled under vacuum. The reaction pH was adjusted to 6.0-7.0 by adding4N HCl. The precipitated solid was collected by filtration, washed with water(50 mL) and dried to give white solid compound 7a. Yield: 5.71 g, 87 %; 1HNMR (CDCl3, 400 MHz, δ inppm): 14.817 (s, 1H, -SH), 9.193 (bs, 1H, Ar-H), 8.793 (s, 1H, Ar-H), 8.764 (s,1H, Ar-H); 13C NMR (100 MHz, CDCl3) δ (ppm): 168.7, 164.2, 152.6, 147.7, 145.4, 143.5; ESI-MS (m/z)= 181.1 (M+H)+; calculated for C6H4N4OS;C, 39.99; H, 2.24; N, 31.09; S, 17.80. Found: C, 39.97; H, 2.25; N, 31.05; S,17.84.
References:
Reddyrajula, Rajkumar;Dalimba, Udayakumar [Bioorganic and Medicinal Chemistry Letters,2020,vol. 30,# 2,art. no. 126846] Location in patent:supporting information
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