ChemicalBook CAS DataBase List Gimeracil

Gimeracil synthesis

5synthesis methods

Product Name:Gimeracil
CAS Number:103766-25-2
Molecular formula:C5H4ClNO2
Molecular Weight:145.54

103792-80-9

103766-25-2

Compound 6 (8.0 g, 44 mmol) was used as a raw material, which was mixed with acetonitrile (100 mL), acetic acid (3 mL) and sodium iodide (13.2 g, 88 mmol), and the reaction was heated at 60°C for 8 hours. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 10% sodium thiosulfate solution (200 mL) to precipitate a colorless solid. Purification by aqueous recrystallization afforded the target product 5-chloro-4-hydroxypyridin-2(1H)-one (Compound 2) in a yield of 5.6 g in 86%. The product characterization data were as follows: melting point 272-273 °C (literature value 273-274 °C); 1H NMR (400 MHz, DMSO-d6) δ 5.70 (s, 1H), 7.51 (s, 1H), 11.29 (br, 2H); 13C NMR (100 MHz, DMSO-d6) δ 163.5, 163.2, 134.6 , 105.6, 98.7; LRMS (ESI) m/z (%): 146 (100) [M(35Cl)+H]+, 148 (30) [M(37Cl)+H]+; HRMS (ESI) m/z calculated value of C5H535ClNO2: [M+H]+: 146.0003, measured value: 146.0012; C5H537ClNO2: [M+H]+: 147.9975, measured value: 147.9975.

103792-80-9 Synthesis

103792-80-9
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103766-25-2
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Yield:103766-25-2 86%

Reaction Conditions:

with acetic acid;sodium iodide in acetonitrile at 60; for 8 h;

Steps:

Synthesis of 5-chloro-2,4-dihydroxypyridine (2):
A mixture of compound 6 (8.0 g, 44 mmol), acetonitrile (100 mL), acetic acid (3 mL)and sodium iodide (13.2 g, 88 mmol) was heated for 8 h at 60 °C. Then the mixture was cooled to room temperature and poured into 10% sodium thiosulfate solution (200 mL) to precipitate a colourless solid, which was recrystallised from water to give pure compound 2: Yield 5.6 g (86%); m.p.272-273 °C (lit.7 273-274 °C); 1H NMR (400 MHz, DMSO-d6): δ 5.70(s, 1H), 7.51 (s, 1H), 11.29 (br, 2H) ; 13C NMR (100 MHz, DMSO-d6): δ163.5, 163.2, 134.6, 105.6, 98.7; LRMS (ESI) m/z (%): 146 (100) [M (35Cl+ 1]+, 148 (30) [M (37Cl) + 1]+; HRMS (ESI) m/z calcd for C5H535ClNO2:[M + H]+: 146.0003; found: 146.0012; calcd for C5H537ClNO2: [M + H]+:147.9975; found: 147.9975.

References:

Li, Xiao-Lin;Zhu, Hao-Ting;Zhan, Li;Liu, Ting;Cheng, Guang;Liu, Ning;Yu, Shan-Bao;Li, Hui;Luo, Yu;Yang, Fan;Tang, Jie [Journal of Chemical Research,2018,vol. 42,# 1,p. 33 - 34]

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26452-80-2 Synthesis