* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
General procedure: These compounds 4a-f were prepared using the general methoddescribed by Gududuru et al. [35]. Sodium hydroxide solution (1 M,2.5 mL) was added to a solution of (12a-f), 40-175 mg, in methanol(2.5 mL) at 0 °C. The solution was stirred for 2 h, and then themethanol was evaporated in vacuo. The solutionwas acidified withconc HCl and extracted with EtOAc (3 50 mL). The combinedorganic layers were washed with water (50 mL) and brine (50 mL),then dried over Na2SO4, filtered and evaporated in vacuo to affordthe corresponding carboxylic acid derivatives 4a-f.
Reference:
[1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 462 - 479
2
[ 57677-79-9 ]
[ 57677-80-2 ]
Yield
Reaction Conditions
Operation in experiment
85%
With potassium hydroxide In methanol for 9 h; Reflux
KOH (0.83 g) was added to a solution of compound 4 (1 g) in anhydrous methanol (15 mL) and refluxed for 9 h. After reaction, the solution was neutralised to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain compound 5 as a white solid: yield:85percent; m.p. 157–159 °C; 1H NMR (500 MHz, CDCl3): δ 8.20 (s, 1H),7.93 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H), 3.88 (s, 3H); 13C NMR(126 MHz, CDCl3): δ 169.0, 162.3, 162.0, 146.5, 128.5, 126.8, 125.1,114.5, 55.5. HRMS (ESI) m/z calcd for C11H9NNaO3S [M + Na]+:258.0195; found: 258.0202.
Reference:
[1] Journal of Chemical Research, 2018, vol. 42, # 7, p. 366 - 370
[2] Justus Liebigs Annalen der Chemie, 1975, p. 1618 - 1624
3
[ 67-56-1 ]
[ 57677-79-9 ]
[ 57677-80-2 ]
Reference:
[1] Journal of Molecular Structure, 2018, vol. 1173, p. 81 - 91
4
[ 25984-63-8 ]
[ 57677-80-2 ]
Reference:
[1] Journal of Molecular Structure, 2018, vol. 1173, p. 81 - 91
[2] Journal of Chemical Research, 2018, vol. 42, # 7, p. 366 - 370
5
[ 2362-64-3 ]
[ 57677-80-2 ]
Reference:
[1] Justus Liebigs Annalen der Chemie, 1975, p. 1618 - 1624
With potassium hydroxide; In methanol; for 9.0h;Reflux;
KOH (0.83 g) was added to a solution of compound 4 (1 g) in anhydrous methanol (15 mL) and refluxed for 9 h. After reaction, the solution was neutralised to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain compound 5 as a white solid: yield:85%; m.p. 157-159 C; 1H NMR (500 MHz, CDCl3): delta 8.20 (s, 1H),7.93 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.4 Hz, 2H), 3.88 (s, 3H); 13C NMR(126 MHz, CDCl3): delta 169.0, 162.3, 162.0, 146.5, 128.5, 126.8, 125.1,114.5, 55.5. HRMS (ESI) m/z calcd for C11H9NNaO3S [M + Na]+:258.0195; found: 258.0202.
General procedure: The target compounds (5a-5c) were synthesized according toScheme 1. A mixture of para-hydroxythiobenzamide (1) (3.93 g, 25.67 mmol) and ethyl bromopyruvate (2) (5.00 g, 25.64 mmol) were combined in ethanol (50 mL). The reaction mixture was refluxed for 4 h, after which the reaction mixture was cooled anddistilled water (100 mL) was added to it. The precipitated solid was filtered and washed with distilled water (50 mL), dried under reduced pressure to obtain ethyl 2-(4-hydroxyphenyl)thiazole-4-carboxylate (3) as a white solid. Compound 3 (1.00 g, 4.02 mmol) was combined with methyl iodide (8.04 mmol), K2CO3 (1.11 g,8.04 mmol) and DMF (8 mL). The reaction mixture was heat to 40 Cfor 8 h. The reaction mixture was cooled and DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (50 mL), filtered and evaporated under reduced pressure to yield the crude product that was purified by column chromatography using petroleum ether and ethyl acetate (4:1) as an eluent toobtain <strong>[57677-79-9]2-(4-methoxyphenyl)thiazole-4-carboxylate</strong> (4) as white solid. KOH (0.83 g) was added in to the solution of compound 4 (1 g) in 15 mL anhydrous methanol and reflux for 9 h. After reaction, the solution was neutralized to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain the 2-(4-methoxyphenyl)thiazole-4-carboxylic acid. Sulfoxide chloride (0.45 mL) was added to the solution of 2-(4-methoxyphenyl)thiazole-4-carboxylic acid (0.4 g) in the dichloromethane (10 mL) and reflux for 10 h. When the reaction was completed, solvent was evaporated under reduced pressure. The residual mass was dissolved into dichloromethane (10 mL). Then the amine was added tothe solution and reflux for another 6 h. When the reaction was finished, the solvent was evaporated under reduced pressure. The residual was purified using column chromatograph (CH2Cl2:CH3OH 15:1) to get 2-phenylthiazole derivatives 5a-c. The forming compounds were grown at room temperature from organic solvent (methanol and dichloromethane) for single crystals of compounds 5a-5c, respectively.
N,N-diethyl-2-(4-methoxyphenyl)thiazole-4-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
51%
General procedure: The target compounds (5a-5c) were synthesized according toScheme 1. A mixture of para-hydroxythiobenzamide (1) (3.93 g, 25.67 mmol) and ethyl bromopyruvate (2) (5.00 g, 25.64 mmol) were combined in ethanol (50 mL). The reaction mixture was refluxed for 4 h, after which the reaction mixture was cooled anddistilled water (100 mL) was added to it. The precipitated solid was filtered and washed with distilled water (50 mL), dried under reduced pressure to obtain ethyl 2-(4-hydroxyphenyl)thiazole-4-carboxylate (3) as a white solid. Compound 3 (1.00 g, 4.02 mmol) was combined with methyl iodide (8.04 mmol), K2CO3 (1.11 g,8.04 mmol) and DMF (8 mL). The reaction mixture was heat to 40 Cfor 8 h. The reaction mixture was cooled and DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (50 mL), filtered and evaporated under reduced pressure to yield the crude product that was purified by column chromatography using petroleum ether and ethyl acetate (4:1) as an eluent toobtain 2-(4-methoxyphenyl)thiazole-4-carboxylate (4) as white solid. KOH (0.83 g) was added in to the solution of compound 4 (1 g) in 15 mL anhydrous methanol and reflux for 9 h. After reaction, the solution was neutralized to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain the <strong>[57677-80-2]2-(4-methoxyphenyl)thiazole-4-carboxylic acid</strong>. Sulfoxide chloride (0.45 mL) was added to the solution of <strong>[57677-80-2]2-(4-methoxyphenyl)thiazole-4-carboxylic acid</strong> (0.4 g) in the dichloromethane (10 mL) and reflux for 10 h. When the reaction was completed, solvent was evaporated under reduced pressure. The residual mass was dissolved into dichloromethane (10 mL). Then the amine was added tothe solution and reflux for another 6 h. When the reaction was finished, the solvent was evaporated under reduced pressure. The residual was purified using column chromatograph (CH2Cl2:CH3OH 15:1) to get 2-phenylthiazole derivatives 5a-c. The forming compounds were grown at room temperature from organic solvent (methanol and dichloromethane) for single crystals of compounds 5a-5c, respectively.
N-cyclohexyl-2-(4-methoxyphenyl)thiazole-4-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
78.1%
General procedure: The target compounds (5a-5c) were synthesized according toScheme 1. A mixture of para-hydroxythiobenzamide (1) (3.93 g, 25.67 mmol) and ethyl bromopyruvate (2) (5.00 g, 25.64 mmol) were combined in ethanol (50 mL). The reaction mixture was refluxed for 4 h, after which the reaction mixture was cooled anddistilled water (100 mL) was added to it. The precipitated solid was filtered and washed with distilled water (50 mL), dried under reduced pressure to obtain ethyl 2-(4-hydroxyphenyl)thiazole-4-carboxylate (3) as a white solid. Compound 3 (1.00 g, 4.02 mmol) was combined with methyl iodide (8.04 mmol), K2CO3 (1.11 g,8.04 mmol) and DMF (8 mL). The reaction mixture was heat to 40 Cfor 8 h. The reaction mixture was cooled and DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (50 mL), filtered and evaporated under reduced pressure to yield the crude product that was purified by column chromatography using petroleum ether and ethyl acetate (4:1) as an eluent toobtain 2-(4-methoxyphenyl)thiazole-4-carboxylate (4) as white solid. KOH (0.83 g) was added in to the solution of compound 4 (1 g) in 15 mL anhydrous methanol and reflux for 9 h. After reaction, the solution was neutralized to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain the <strong>[57677-80-2]2-(4-methoxyphenyl)thiazole-4-carboxylic acid</strong>. Sulfoxide chloride (0.45 mL) was added to the solution of <strong>[57677-80-2]2-(4-methoxyphenyl)thiazole-4-carboxylic acid</strong> (0.4 g) in the dichloromethane (10 mL) and reflux for 10 h. When the reaction was completed, solvent was evaporated under reduced pressure. The residual mass was dissolved into dichloromethane (10 mL). Then the amine was added tothe solution and reflux for another 6 h. When the reaction was finished, the solvent was evaporated under reduced pressure. The residual was purified using column chromatograph (CH2Cl2:CH3OH 15:1) to get 2-phenylthiazole derivatives 5a-c. The forming compounds were grown at room temperature from organic solvent (methanol and dichloromethane) for single crystals of compounds 5a-5c, respectively.
(3,5-dimethylpiperidin-1-yl)(2-(4-methoxyphenyl)thiazol-4-yl)methanone[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
72%
General procedure: The target compounds (5a-5c) were synthesized according toScheme 1. A mixture of para-hydroxythiobenzamide (1) (3.93 g, 25.67 mmol) and ethyl bromopyruvate (2) (5.00 g, 25.64 mmol) were combined in ethanol (50 mL). The reaction mixture was refluxed for 4 h, after which the reaction mixture was cooled anddistilled water (100 mL) was added to it. The precipitated solid was filtered and washed with distilled water (50 mL), dried under reduced pressure to obtain ethyl 2-(4-hydroxyphenyl)thiazole-4-carboxylate (3) as a white solid. Compound 3 (1.00 g, 4.02 mmol) was combined with methyl iodide (8.04 mmol), K2CO3 (1.11 g,8.04 mmol) and DMF (8 mL). The reaction mixture was heat to 40 Cfor 8 h. The reaction mixture was cooled and DMF was evaporated under reduced pressure. The residue was extracted with ethyl acetate (50 mL), filtered and evaporated under reduced pressure to yield the crude product that was purified by column chromatography using petroleum ether and ethyl acetate (4:1) as an eluent toobtain 2-(4-methoxyphenyl)thiazole-4-carboxylate (4) as white solid. KOH (0.83 g) was added in to the solution of compound 4 (1 g) in 15 mL anhydrous methanol and reflux for 9 h. After reaction, the solution was neutralized to pH 5 and poured into cool water (100 mL). The residue was filtered and dried to obtain the 2-(4-methoxyphenyl)thiazole-4-carboxylic acid. Sulfoxide chloride (0.45 mL) was added to the solution of 2-(4-methoxyphenyl)thiazole-4-carboxylic acid (0.4 g) in the dichloromethane (10 mL) and reflux for 10 h. When the reaction was completed, solvent was evaporated under reduced pressure. The residual mass was dissolved into dichloromethane (10 mL). Then the amine was added tothe solution and reflux for another 6 h. When the reaction was finished, the solvent was evaporated under reduced pressure. The residual was purified using column chromatograph (CH2Cl2:CH3OH 15:1) to get 2-phenylthiazole derivatives 5a-c. The forming compounds were grown at room temperature from organic solvent (methanol and dichloromethane) for single crystals of compounds 5a-5c, respectively.
General procedure: These compounds 4a-f were prepared using the general methoddescribed by Gududuru et al. [35]. Sodium hydroxide solution (1 M,2.5 mL) was added to a solution of (12a-f), 40-175 mg, in methanol(2.5 mL) at 0 C. The solution was stirred for 2 h, and then themethanol was evaporated in vacuo. The solutionwas acidified withconc HCl and extracted with EtOAc (3 50 mL). The combinedorganic layers were washed with water (50 mL) and brine (50 mL),then dried over Na2SO4, filtered and evaporated in vacuo to affordthe corresponding carboxylic acid derivatives 4a-f.