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Preparation method of environmental-friendly high-purity 2,4,6-trichloropyrimidine

A trichloropyrimidine, high-purity technology, applied in the field of synthetic high-purity 2, can solve problems affecting application, poor catalytic performance, etc., and achieve the effects of easy operation, high selectivity and high yield

Inactive Publication Date: 2011-02-16
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the poor selective catalytic performance of the catalyst, the obtained product contains a certain amount of tetrachloropyrimidine by-products, which affects the application of this product in pharmaceutical synthesis.

Method used

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  • Preparation method of environmental-friendly high-purity 2,4,6-trichloropyrimidine
  • Preparation method of environmental-friendly high-purity 2,4,6-trichloropyrimidine
  • Preparation method of environmental-friendly high-purity 2,4,6-trichloropyrimidine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Weigh 1.28g of barbituric acid and put it into a 50mL dry ground-mouthed round-bottom flask, pipette 1.7mL of composite catalyst (wherein N, N-diethylaniline 1.4mL, N, N-dimethylaniline 0.1 mL, quinoline 0.2mL), added to the round bottom flask, then pipette 2.8mL of phosphorus oxychloride with a pipette, added to the round bottom flask, put the stirring bar; install the serpentine condenser and drying tube, and Pass in cooling water, stir with DF-101B constant temperature magnetic stirrer and heat to 138°C. After reacting for 4 hours, distill the reaction solution with water vapor under reduced pressure, and the distillate is cooled to precipitate solids, filtered, rinsed with water, and dried to obtain white The massive solid is the target compound 2,4,6-trichloropyrimidine. The yield was 91.2%.

[0033] 1 HNMR (400MHz, CDCl 3 ): δ (ppm): 7.45 (s, H,);

[0034] 13 CNMR (100MHz, CDCl 3 ): δ (ppm): 162.88 (C2, C6); 160.10 (C4); 120.04 (C1);

[0035] IR(KBr):v(cm ...

Embodiment 2

[0038] Weigh 1.28g of barbituric acid and put it into a 50mL dry ground-mouthed round-bottom flask, pipette 1.7mL of composite catalyst (wherein N, N-diethylaniline 1.4mL, N, N-dimethylaniline 0.1 mL, quinoline 0.2mL) into the round-bottomed flask, then pipette 2.8mL of phosphorus oxychloride into the round-bottomed flask, and put in a stirring bar. Install serpentine condensing tube and drying tube, and pass in cooling water, stir with DF-101B constant temperature magnetic stirrer and heat to 110°C, after 0.5h of reaction, distill the reaction solution with water vapor under reduced pressure, and cool the distillate to precipitate solid , filtered, rinsed with water, and dried to obtain a white blocky solid which is the target compound 2,4,6-trichloropyrimidine. The yield is 82.87%.

[0039] 1 HNMR (400MHz, CDCl 3 ): δ (ppm): 7.45 (s, H,);

[0040] 13 CNMR (100MHz, CDCl 3 ): δ (ppm): 162.88 (C2, C6); 160.10 (C4); 120.04 (C1);

[0041] IR(KBr):v(cm -1 ): 3108.63(m); 15...

Embodiment 3

[0044] Weigh 1.28g of barbituric acid and put it into a 50mL dry ground-mouthed round-bottom flask, pipette 1.7mL of composite catalyst (wherein N, N-diethylaniline 1.4mL, N, N-dimethylaniline 0.1 mL, quinoline 0.2mL) into the round-bottomed flask, then pipette 2.8mL of phosphorus oxychloride into the round-bottomed flask, and put in a stirring bar. Install a serpentine condenser tube and a drying tube, and pass in cooling water, stir with a DF-101B constant temperature magnetic stirrer and heat to 90°C. After reacting for 3 hours, distill the reaction solution with water vapor under reduced pressure, and cool the distillate to precipitate solids. Filter, rinse with water, and dry to obtain a white blocky solid which is the target compound 2,4,6-trichloropyrimidine. The yield was 82%.

[0045] 1 HNMR (400MHz, CDCl 3): δ (ppm): 7.45 (s, H,);

[0046] 13 CNMR (100MHz, CDCl 3 ): δ (ppm): 162.88 (C2, C6); 160.10 (C4); 120.04 (C1);

[0047] IR(KBr):v(cm -1 ): 3108.63(m); 15...

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Abstract

The invention provides a synthetic method for high-purity 2,4,6-trichloropyrimidine, which comprises the steps of: taking barbituric acid as the raw material and phosphorus oxychloride as a chlorinated agent, catalyzing the material by a compound catalyst of N, N-diethylaniline, N, N-dimethylaniline and quinoline; reacting for 0.5-4h at 90-140 DEG C; carrying out pressure reduction, distillation and separation by water vapor; cooling and separating out solid; filtering, washing, and drying to obtain the white lumpy solid of the 2, 4, 6-trichloropyrimidine with purity of more than 99.52 and yield of 80-92 percent. The preparation method has the advantages of non-toxic, cheap, easily-obtaining and mutually dissolved reaction materials without using organic solvents, simple reaction processing and easy operation due to the adoption of one-step synthesis, no waste gas emission in the entire reaction process, no waste residual, recycled catalyst after the separation from the reaction wasteliquid, and lower cost. In addition, the separated waste liquid can be manufactured into calcium-magnesia phosphate fertilizer, thereby realizing the recovery of the waste liquid and conforming to theidea of green synthesis simultaneously.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a preparation method of 2,4,6-trichloropyrimidine, in particular to a preparation method of 2,4,6-trichloropyrimidine, which uses barbituric acid as a raw material, phosphorus oxychloride as a chlorination agent, and is catalyzed by a compound catalyst. Next, a method for synthesizing high-purity 2,4,6-trichloropyrimidine. Background technique [0002] Pyrimidine and its derivatives are an important class of pharmaceutical and active fuel intermediates, mainly used in the synthesis of antimicrobial infection drugs, hypnotic and sedative drugs, and the synthesis of active fuels. 2,4,6-Trichloropyrimidine, as an intermediate of pharmaceuticals and reactive dyes, is in great demand and requires high purity. [0003] At present, the production of 2,4,6-trichloropyrimidine usually uses malonic acid and urea as raw materials, and under the catalysis of sodium ethylate, first ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/30B01J31/02
CPCY02P20/584
Inventor 秦淑琪牛克彦王建明杨武
Owner NORTHWEST NORMAL UNIVERSITY
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