Preparation method of TTZ (thiotriazinone)

A technology of methylthiosemicarbazide and hydroxyl, which is applied in the field of preparation of cephalosporin intermediates, can solve the problems of difficult solvent recovery, unstable quality, large amount of waste water, etc., to reduce the cost of solvent recovery, reduce side reactions, and yield Improved effect

Active Publication Date: 2014-03-26
SHANDONG HUIHAI PHARMA & CHEM
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Problems solved by technology

[0005] The technical problem to be solved by the present invention is to provide a preparation method of 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1,2,4-triazine (TTZ), Overcome the common problems of high cost, low yield and large fluctuation, unstable quality, difficult solvent recovery and large amount of waste water in the existing technology

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 2000kg of ethanol, 480kg of 2-methylthiosemicarbazide, 10kg of acetic acid, 100g of ammonium acetate, 21.6kg of catalyst boron tribromide, and 800kg of diethyl oxalate into the 5000L reactor. After the dropwise addition, heat up to 80°C Insulate for 4 hours, after the reaction, cool down to 15°C and filter to obtain the crude triazine ring (wet weight 10%) and mother liquor. Put the crude product into the refining reactor, add 2000kg of water, heat up to 78°C, add 1300kg of hydrochloric acid with a concentration of 30%, and cool down to 10 ℃, after centrifuge filter and dry, the finished product is 564kg, the yield is 77.63%, and the purity is 99.96%.

[0025] Gained mother liquor is applied mechanically 5 times continuously, and data is as follows:

[0026] Mother liquor cycle times Product weight / kg Product yield / % purity / % 0 564 77.63% 99.96% 1 570 78.35% 99.89% 2 567 78% 99.90% 3 567 78% 99.85% 4 565 77.75% 99.82...

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Abstract

The invention discloses a preparation method of TTZ (thiotriazinone), which comprises the following steps: 1) adding 5-10 kg of acetic acid and 50-150 kg of ammonium acetate into 1,800-2,200 kg of ethyl alcohol to prepare a buffer system with the pH value of 6-7; 2) adding 480-500 kg of 2-methyl-3-thiosemicarbazide, boron tribromide and diethyl oxalate, heating to 80-82 DEG C, and performing circulation reflux reaction for 4-6 hours, wherein the molar ratio of 2-methyl-3-thiosemicarbazide to diethyl oxalate is 1:(1.15-1.25), and the dosage of boron tribromide is 4-6% of the weight of 2-methyl-3-thiosemicarbazide; 3) cooling for crystallization, and separating to obtain a TTZ crude product and a mother liquor; 4) adding 1,800-2,200 kg of water in the TTZ crude product, heating to 70-80 DEG C, then adding 1,250-1,400 kg of hydrochloric acid with the concentration of 30%, cooling for crystallization, separating and drying to obtain the TTZ finished product. The preparation method has the advantages that the common problems of high cost, low yield, large yield variability, instability of product quality, difficulty in solvent recovery, large amount of waste water and the like in the prior art can be solved.

Description

technical field [0001] The present invention relates to a preparation method of cephalosporin intermediates, more specifically to a 2,5-dihydro-6-hydroxyl-2-methyl-5-oxo-3-mercapto-1,2,4 - Process for the preparation of triazines (TTZ). Background technique [0002] 2,5-Dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1,2,4-triazine (TTZ) is a white crystal, mainly used as an intermediate in the production of ceftriaxone body. At present, the method of large-scale production of 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1,2,4-triazine (TTZ) at home and abroad is to use 2-methyl After the reaction of thiosemicarbazide, diethyl oxalate and sodium methoxide, triazine ring sodium salt is generated, and then hydrochloric acid is added to obtain 2,5-dihydro-6-hydroxy-2-methyl-5-oxo-3-mercapto-1 , the method of 2,4-triazine, but its shortcomings are obvious, mainly: 1. The product yield is low and the quality is unstable; 2. Sodium methoxide is used as an alkali catalyst and a r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/07
CPCC07D253/075
Inventor 郭刚张忠政李新忠张世凤
Owner SHANDONG HUIHAI PHARMA & CHEM
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