3-Pyridinecarboxylic acid, 5-cyano-6-[(cyanomethyl)thio]-4-(4-methoxyphenyl)-2-methyl-, ethyl ester synthesis
- Product Name:3-Pyridinecarboxylic acid, 5-cyano-6-[(cyanomethyl)thio]-4-(4-methoxyphenyl)-2-methyl-, ethyl ester
- CAS Number:924272-36-6
- Molecular formula:C19H17N3O3S
- Molecular Weight:367.42
Yield:924272-36-6 92%
Reaction Conditions:
with anhydrous Sodium acetate in ethanol at 20; for 3 h;
Steps:
4-Aryl-3-cyano-2-cyanomethylthio-5-ethoxycarbonyl-6-methylpyridines (3a,b).
General procedure: To a suspension of compound2a,b (10 mmol) and sodium acetate trihydrate (1.36 g, 10 mmol) in ethanol (40. mL), chloroacetonitrile (0.64mL, 10 mmol) was added. The resulting mixture was stirred at room temperature for 3 h. The white precipitatethat formed was collected and recrystallized from ethanol to give 4a,b.3-Cyano-2-cyanomethylthio-5-ethoxycarbonyl-4-(4-methoxyphenyl)-6-methylpyridine (3a). Prepared aswhite needles in 92% yield; mp 121-122 °C. IR (KBr) cm-1: 2250 (C≡N, non conjugated), 2220 (C≡N,conjugated), 1731 (C=O); 1H NMR (400 MHz, CDCl3) d ppm: 7.30-7.32 (dd, J 2.3 Hz, 2H, Ar-H), 6.97-7.00 (dd, J2.3 Hz, 2H, Ar-H), 4.05-4.11 (q, J 7.0 Hz, 2H, OCH2), 4.07 (s, 2H, SCH2), 3.85 (s, 3H, OCH3), 2.67 (s, 3H, CH3),0.98-1.02 (t, J 7.0 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3) d ppm: 166.6, 161.0, 159.2, 158.8, 152.6, 129.7,126.7, 126.2, 115.8, 114.3, 114.1, 105.1, 61.9, 55.4, 23.4, 15.9, 13.7; MS: m/z 367 (M+, 100%), 352 (M+-CH3,12%), 337 (M+-2CH3, 25%), 322 (M+- OC2H5, 14%). Anal. Calcd. for C19H17N3O3S (367.1)): C, 62.11; H, 4.66; N,11.44; S, 8.73%. Found: C, 62.43; H, 4.49; N, 11.90; S, 8.92%.
References:
Bakhite, Etify A.;Abeed, Ahmed Abdou O.;Ahmed, Ola E.A. [Arkivoc,2017,vol. 2017,# 4,p. 121 - 136]
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