A suspension of compound 5.2 (393 g, 2.35 mol) and potassium o-ethylxanthate (393 g, 2.45 mol) in pyridine (3 L) was heated to reflux for 12 hours. TLC (EtOAc/petroleum ether=1:2) indicated the reaction was complete. The mixture was cooled to room temperature and poured into four 5 L flasks containing 1600 mL on concentrated HCl and 10 L of ice water. The mixture was swirled for 5 minutes and the solid product was recovered by filtration. The solid was washed with 1 L of water and dried for 30 minutes. The solid was dissolved in 10 L ethylacetate, washed with 2 L of 1N HCl and 1 L of brine, dried over Na2SO4 and concentrated to afford compound 5.3 (390g, 79.3percent) as a pink solid.
79.3%
for 12 h; Reflux
A suspension of the ester (393g, 2.35 mol) and potassium o-ethylxanthate (393 g, 2.45 mol) in pyridine (3L) was heated to reflux for 12 hours. TLC (EtOAc/petroleum ether = 1:2) indicated the reaction was complete. The mixture was cooled to room temperature and poured into four 5L flasks containing 1600 mL on concentrated HCl and 10L of ice water. The mixture was swirled for 5 minutes and the solid product was recovered by filtration. The solid was washed with 1L of water and dried for 30 minutes. The solid was dissolved in 10L ethylacetate, washed with 2L of 1N HCl and 1L of brine, dried over Na2SO4 and concentrated to afford (390g, 79.3percent) of a pink solid
56%
at 115℃; for 5 h;
To a stirring solution of methyl 4-amino-3-hydroxybenzoate (5 g, 29.91 mmol) in pyridine (60 mL) was added ethoxy(potassiosulfanyl)methanethione (5 g, 31.19 mmol). The resulting solution was stirred for 5 h at 115°C. The reaction was quenched with water. The resulting solution was extracted with 3x30 mL of dichloromethane. The organic layers were combined and washed successively with water and brine. The residue was concentrated under vacuum after dried over anhydrous sodium sulfate. This resulted in 3.5 g (56percent) of the title compound as a yellow solid.
Reference：
[1] Patent: US2010/305073, 2010, A1, . Location in patent: Page/Page column 21
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4998 - 5002
[3] Patent: WO2018/85148, 2018, A1, . Location in patent: Paragraph 0114
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
2
[ 463-71-8 ]
[ 63435-16-5 ]
[ 72752-81-9 ]
Reference：
[1] Patent: WO2010/56717, 2010, A1, . Location in patent: Page/Page column 41; 42
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4001 - 4013
3
[ 2374-03-0 ]
[ 72752-81-9 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 4998 - 5002
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4001 - 4013
A suspension of compound 5.2 (393 g, 2.35 mol) and potassium o-ethylxanthate (393 g, 2.45 mol) in pyridine (3 L) was heated to reflux for 12 hours. TLC (EtOAc/petroleum ether=1:2) indicated the reaction was complete. The mixture was cooled to room temperature and poured into four 5 L flasks containing 1600 mL on concentrated HCl and 10 L of ice water. The mixture was swirled for 5 minutes and the solid product was recovered by filtration. The solid was washed with 1 L of water and dried for 30 minutes. The solid was dissolved in 10 L ethylacetate, washed with 2 L of 1N HCl and 1 L of brine, dried over Na2SO4 and concentrated to afford compound 5.3 (390g, 79.3%) as a pink solid.
79.3%
With pyridine; for 12h;Reflux;
A suspension of the ester (393g, 2.35 mol) and potassium o-ethylxanthate (393 g, 2.45 mol) in pyridine (3L) was heated to reflux for 12 hours. TLC (EtOAc/petroleum ether = 1:2) indicated the reaction was complete. The mixture was cooled to room temperature and poured into four 5L flasks containing 1600 mL on concentrated HCl and 10L of ice water. The mixture was swirled for 5 minutes and the solid product was recovered by filtration. The solid was washed with 1L of water and dried for 30 minutes. The solid was dissolved in 10L ethylacetate, washed with 2L of 1N HCl and 1L of brine, dried over Na2SO4 and concentrated to afford (390g, 79.3%) of a pink solid
56%
With pyridine; at 115℃; for 5h;
To a stirring solution of methyl 4-amino-3-hydroxybenzoate (5 g, 29.91 mmol) in pyridine (60 mL) was added ethoxy(potassiosulfanyl)methanethione (5 g, 31.19 mmol). The resulting solution was stirred for 5 h at 115C. The reaction was quenched with water. The resulting solution was extracted with 3x30 mL of dichloromethane. The organic layers were combined and washed successively with water and brine. The residue was concentrated under vacuum after dried over anhydrous sodium sulfate. This resulted in 3.5 g (56%) of the title compound as a yellow solid.
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