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A kind of method for preparing bisthiadiazole diamine

A technology of bisthiadiazole diamine and dicarboxylic acid, applied in the direction of organic chemistry, can solve the problems of long reaction time, high equipment requirements, complicated operation, etc., and achieve long reaction time, low equipment requirements, and lower reaction temperature Effect

Active Publication Date: 2016-01-20
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the traditional method for preparing bisthiadiazole diamine is prepared by reflux reaction of dibasic carboxylic acid and thiosemicarbazide under the catalysis of concentrated hydrochloric acid. The reaction time of this method is very long, the operation is complicated, and the equipment requirements are high.

Method used

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  • A kind of method for preparing bisthiadiazole diamine
  • A kind of method for preparing bisthiadiazole diamine
  • A kind of method for preparing bisthiadiazole diamine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 1) Add 0.1mol thiosemicarbazide, 0.055mol malonic acid and 0.055mol phosphorus pentachloride to a dry mortar, and grind for 20 minutes at room temperature. At this time, TLC monitoring shows that the raw material point of malonic acid disappears, indicating that the raw materials are completely reacted , and then left to stand for 1h to obtain crude product; wherein the developer of TLC is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3;

[0029] 2) Move the crude product into a beaker, add a sodium carbonate solution with a mass concentration of 5% to the crude product until the pH of the resulting mixture is 8, filter with suction, dry the filter cake with a volume ratio of 1:2 N,N-dimethylformamide (DMF) and H 2 The mixed solvent of O was recrystallized to obtain bisthiadiazole diamine (n=1 in the structural formula), and the yield was 91.6%.

[0030] IR (KBr tablet): 3244cm -1 ,3176cm -1 (νsN-H,s); 2981cm -1 (saturated C-H stretchin...

Embodiment 2

[0032] 1) Add 0.1mol thiosemicarbazide, 0.055mol succinic acid and 0.055mol phosphorus pentachloride to a dry mortar, and grind for 20 minutes at room temperature. At this time, TLC monitoring shows that the raw material point of succinic acid disappears, indicating that the raw materials are completely reacted , and then left to stand for 1h to obtain crude product; wherein the developer of TLC is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3;

[0033] 2) Move the crude product into a beaker, add a sodium carbonate solution with a mass concentration of 5% to the crude product until the pH of the resulting mixture is 8, filter with suction, dry the filter cake with a volume ratio of 1:2 DMF and H 2 The mixed solvent of O was recrystallized to obtain bisthiadiazole diamine (n=2 in the structural formula), and the yield was 92.3%.

[0034] IR (KBr tablet): 3410cm -1 ,3233cm -1 (νsN-H,s); 2989cm -1 ,2854cm -1 (saturated C-H stretching vibratio...

Embodiment 3

[0036] 1) Add 0.1mol thiosemicarbazide, 0.055mol glutaric acid and 0.055mol phosphorus pentachloride to a dry mortar, and grind for 20 minutes at room temperature. At this time, TLC monitoring shows that the raw material point of glutaric acid disappears, indicating that the raw material is completely reacted , and then left to stand for 1h to obtain crude product; wherein the developer of TLC is a mixed solution of ethyl acetate and sherwood oil with a volume ratio of 1:3;

[0037] 2) Move the crude product into a beaker, add a sodium carbonate solution with a mass concentration of 5% to the crude product until the pH of the resulting mixture is 8, filter with suction, dry the filter cake with a volume ratio of 1:2 DMF and H 2 The mixed solvent of O was recrystallized to obtain bisthiadiazole diamine (n=3 in the structural formula), and the yield was 94.0%.

[0038] IR (KBr tablet): 3239cm -1 ,3213cm -1 (νsN-H,s); 2882cm -1 ,2813cm -1 (saturated C-H stretching vibration)...

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Abstract

The invention discloses a method for preparing bithiadiazole diamine. The method comprises the following steps: adding A mol of thiosemicarbazide, B mol of dicarboxylic acid and C mol of phosphorus pentachloride into a dry reaction container, uniformly grinding at the room temperature, and standing to obtain a crude product, wherein the ratio of A to B and C is 2:(1-1.2):(1-1.2); further adding an alkali solution into the crude product till the pH value of the obtained mixture solution is 8-8.2, subsequently filtering the mixture solution, drying the filter cake and recrystallizing so as to obtain bithiadiazole diamine. The method adopts a solid phase synthesis method, reactants are put into a mortar for direct grinding reaction, the reaction phenomenon is remarkable, the reaction time is short, the reaction condition is gentle, the reaction can be carried out at the room temperature, the equipment requirement is low, phosphorus pentachloride is low in price and low in toxicity, the product yield is as high as more than 92%, and the method is economic, efficient, simple and convenient for preparing bithiadiazole diamine.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing bisthiadiazole diamine. Background technique [0002] Thiadiazole compounds have been widely used in recent years, and they are used in the production of cefazolin, cefkanet, cefazidone, azoxazone cephalosporin, cefopero, cephalosporin BL-S339, furobenazole cephalosporin, etc. It is an important intermediate of medicine, because this kind of medicine has the characteristics of broad-spectrum antibacterial, good absorption, small side effects, especially suitable for oral absorption, etc., so it is widely used in clinical practice. Bitthiadiazole has a double thiadiazole ring, so its medicinal activity is more significant. However, the traditional method for preparing bisthiadiazole diamine is prepared by reflux reaction of dibasic carboxylic acid and thiosemicarbazide under the catalytic action of concentrated hydrochloric acid. The reaction time of this ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/135
CPCC07D285/135
Inventor 刘玉婷刘蓓蓓尹大伟宋思梦王金玉杨阿宁
Owner SHAANXI UNIV OF SCI & TECH