Réaction #937171

Équation de réaction

compound 15

5-ethyl-6-methyl-3-carbethoxy-4-(3', 5'-dimethylphenyl)thio-pyridin-2(1H)-one

compound 7a

5-methyl-3-nitro-4-(3', 5'-dimethylphenyl)thiopyridin-2(1H)-one

3,5-dimethylthiophenol

→

Product 15

4-phenylthiopyridinone

Solvants

ethanol

triethylamine

Conditions de réaction

Traitement

1. 1
   TempératureAfter 12 hours under reflux
2. 2
   Autrethe white precipitate was isolated by filtration
3. 3
   Autrecrystallised in ethyl acetate

Mode opératoire

As for the method described for obtaining compound 7a in example 10, a mixture of compound 15 (1.00 g, 4.1 mmoles) in 10 ml of ethanol and 1 ml of triethylamine was agitated until homogeneous. 3,5-dimethylthiophenol (0.61 ml, 4.5 mmoles) was added. After 12 hours under reflux, the white precipitate was isolated by filtration and crystallised in ethyl acetate. Product 15 was obtained (1.05 g, 82%) in the form of white crystals: melting point 202° C.; NMR-1H (DMSO-d6) δ 12.17 (1H, s, NH-1), 7.22 (1H, s, H-4'), 6.92 (1H, s, H-2' and 6'), 4.09 (2H, q, J=7 Hz, COOCH2CH3), 2.45 (2H, q, J=7 Hz, CH2CH3), 2.27 (3H, s, CH3 -6), 2.25 (6H, s, CH3 -3' and 5'), 1.15 (3H, t, j=7 Hz, COOCH2CH3), 0.85 (3H, t, J=7 Hz, CH2CH3). Anal. C19H23NO3S (C, H, N, S).

Source