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ChemicalBook CAS DataBase List Thiotriazinone
58909-39-0

Thiotriazinone synthesis

1synthesis methods
2-Methyl-3-thiosemicarbazide

6938-68-7

Diethyl oxalate

95-92-1

Thiotriazinone

58909-39-0

General procedure for the synthesis of triazine ring from 2-methylaminothiourea and diethyl oxalate: 2-methylaminothiourea, mixed solvent (1:3 mass ratio of methanol to DMSO), diethyl oxalate and sodium methanolate were added to the reactor in the mass ratio 1:10:4:10. The cyclization reaction was carried out in the temperature range of 0-45°C. Upon completion of the reaction, acidification was carried out with hydrochloric acid in an amount of 30% by mass of 2-methylaminothiourea. Subsequently, the reaction mixture was filtered and dried to give the triazine ring in 91.6% yield. The purity of the product was assayed by HPLC and the by-product content was 0.0005% (5 ppm). The product was calculated as M (triazine ring) / [M (methylaminothiourea) * 159.17 / 105.16].

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Yield:58909-39-0 92.7%

Reaction Conditions:

with dmap;N,N,N,N,-tetramethylethylenediamine;sodium methylate in methanol;ethanol at 15 - 55; for 4 h;Temperature;Solvent;Reagent/catalyst;

Steps:

1-3; 1-5 Example 1
Add 10.5g of 2-methylthiosemicarbazide, 15.3g of diethyl oxalate, 31.5g of methanol, and 31.5g of ethanol to the reaction flask, reduce to 15°C, and add mixed alkali catalyst (including 36.8g of sodium methoxide, 0.05g of DMAP, TMEDA 0.05g) 1.5h, after dripping, heat up to 55 for cyclization reaction for 2.5h, acidify with hydrochloric acid to pH=1.0, cool down to 5 and filter with suction to obtain crude thiotriazinone ring, which is dissolved in 63g distilled water at 70 and cooled Crystallize at 15°C and filter with suction to obtain a wet product of thiotriazinone ring, and dry at 100°C for 3 hours to obtain 14.75 g of dry product of thiotriazinone ring, with a purity of 99.6% and a yield of 92.7%.

References:

CN112759558, 2021, A Location in patent:Paragraph 0017; 0035-0050

FullText

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