5-ACETYL-2-MERCAPTO-6-METHYLNICOTINONITRILE synthesis
- Product Name:5-ACETYL-2-MERCAPTO-6-METHYLNICOTINONITRILE
- CAS Number:165283-95-4
- Molecular formula:C9H8N2OS
- Molecular Weight:192.24
7357-70-2
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Yield:165283-95-4 97%
Reaction Conditions:
Stage #1: acetylacetonewith N,N-dimethyl-formamide dimethyl acetal in 1,4-dioxane at 20;Inert atmosphere;
Stage #2: Cyanothioacetamidewith sodium methylate;sodium in methanol at 20; for 1 h;Inert atmosphere;
Steps:
5-Acetyl-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile23
Amixture of acetylacetone 22 (1.00mL, 10.0 mmol) and N,N-dimethylformamide dimethylacetal (1.33 mL, 10.0 mmol) in drydioxane (10.0 mL) was stirred under an atmosphere of nitrogen at r.t.overnight. A second mixture of sodium methoxide was prepared by adding sodium(0.46 g, 20.0 mmol) to dry methanol (10.5 mL, 0.260 mol). Cyanothioacetamide(1.00 g, 10.0 mmol) was added to the sodium methoxide and stirred for 10 min,after which the second mixture was added to the first and stirred for 1 h atr.t.. This was followed by heating at reflux for 4 h. After cooling, themixture was acidified with ice cold 2 M HCl and water added. The resultingsolid was collected by filtration to give the title compound 23 (1.86 g, 97%) as a light brown solid. m.p.200-202 °C (lit. 230-232 °). δH (400 MHz, (CD3)2SO)2.51 (3H, s, COCH3), 2.64 (3H, s, 6-CH3), 8.55 (1H, s,H-4), 14.26 (1H, br s, NH). δC (100 MHz, (CD3)2SO) 19.5 (6-CH3),29.0 (COCH3), 113.3 (C-3), 116.6 (3-CN), 121.1 (C-5), 145.0(C-4), 157.4 (C-6), 179.2 (C-2), 195.5 (COCH3). νmax(ATR)/cm-1 3423, 3191, 3021, 2228, 1662, 1589, 1494, 1366, 1267,1174. m/z (ESI+): 215 (MNa+, 25%), 163 (55%), 101 (100%). HRMS (ESI+) found (MNa+):215.0243 C9H8N2NaOS requires 215.0250. The 1H NMR values were in agreementwith literature values
References:
van Rensburg, Michelle;Leung, Euphemia;Haverkate, Natalie A.;Eurtivong, Chatchakorn;Pilkington, Lisa I.;Reynisson, Jóhannes;Barker, David [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 2,p. 135 - 138] Location in patent:supporting information
7357-70-2
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4637-24-5
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![2,4-Pentanedione, 3-[(dimethylamino)methylene]-](/CAS/GIF/18856-72-9.gif)
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33884-41-2
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165283-95-4
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123-54-6
566 suppliers
$10.00/25ml
165283-95-4
14 suppliers
inquiry