ChemicalBook CAS DataBase List 7,8-dihydro-2-(Methylthio)quinazolin-5(6H)-one

7,8-dihydro-2-(Methylthio)quinazolin-5(6H)-one synthesis

4synthesis methods

Product Name:7,8-dihydro-2-(Methylthio)quinazolin-5(6H)-one
CAS Number:21599-35-9
Molecular formula:C9H10N2OS
Molecular Weight:194.25

2-[(Dimethylamino)methylene]-1,3-cyclohexanedione

85302-07-4
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867-44-7
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$5.00/10g

7,8-dihydro-2-(Methylthio)quinazolin-5(6H)-one

21599-35-9
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$45.00/10mg

Yield:21599-35-9 90%

Reaction Conditions:

with sodium carbonate in 1,4-dioxane; for 8 h;Reflux;

Steps:

2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one (9)

A mixture of compounds 2 (20 g, 120 mmol), sodium carbonate (15.2 g, 144 mmol) and the S-methyllisothiourea sulfate (27.11 g, 144 mmol) was added in 1,4-dioxane (450 mL). The reaction solution was refluxed for 8 h. After completion of the reaction as monitored by TLC, the mixture was cooled to room temperature. Water was added drop by drop, giving a precipitate, which was collected, and purified by flash column chromatography (petroleum ether/ethyl acetate, 8:1 v/v) to afford pure product 9. White solid. Yield: 90%; ¹H NMR (400 MHz, DMSO) δ: 9.19 (s, 1H, -CH), 3.15 (t, J = 6.2 Hz, 2H, -CH₂), 2.92 (s, 3H, -SCH₃), 2.74 (t, J = 6.2 Hz, 2H, -CH₂), 2.17 (m, 2H, -CH₂); ¹³C NMR (100 MHz, DMSO) δ: 196.00, 175.80, 166.44, 159.63, 121.32, 55.75, 38.18, 31.91, 21.09; HRMS calculated for C₉H₁₀N₂OS 195.0592 [M+H]⁺, found 195.0581.

References:

Hu, Xiaoxia;Zhao, Hui;Wang, Youzhi;Liu, Zhan;Feng, Bainian;Tang, Chunlei [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 20,p. 3385 - 3390] Location in patent:supporting information

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2986-19-8 Synthesis