Method for preparing thiobarbituric acid compound

A technology of thiobarbituric acid and compounds, applied in the direction of organic chemistry, can solve the problems of high yield and low yield, and achieve the effects of high yield, simple production, and easy factory operation

Active Publication Date: 2014-08-20
CHONGQING HUABANGSHENGKAI PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above-mentioned reasons, the present invention provides a kind of new method, adopts formula II to be that raw material and thiourea and aluminum isop

Method used

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  • Method for preparing thiobarbituric acid compound

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0035] Example 1 Preparation of 4,6-dihydroxy-2-mercaptopyrimidine (using diethyl malonate as raw material)

[0036] The chemical reaction is as follows:

[0037]

[0038] Specifically: add 152.2g (2mol) of thiourea and 2000ml of ethanol into the reactor, and heat to about 50℃ to dissolve; add 160.2g (1mol) of diethyl malonate, and raise the temperature to 60~70℃; within 1 hour After adding 20.4g (0.1mol) of aluminum isopropoxide, react at 70~80℃ for 4 hours; slowly cool to 10~20℃, stir for 1 hour, filter; then heat to dissolve with 800ml of water, cool 0~10℃, add hydrochloric acid to acidify pH is 5-7, stirred for 1 hour and filtered; dried under vacuum to obtain 130.7g. The yield is 94.6%, and the content is 98.8%.

Example Embodiment

[0044] Example 2 Preparation of 4,6-dihydroxy-5-nitro-2-mercaptopyrimidine (using 1-ethyl 3-methyl 2-nitromalonate diester as raw material)

[0045] The chemical reaction formula is as follows:

[0046]

[0047] Add 761g (10mol) of thiourea and 2000ml of isopropanol to the reactor, heat to about 50℃ to dissolve; add 191.1g (1mol) of 1-ethyl 3-methyl 2-nitromalonic acid diester, control the temperature -10~20℃; add 204.3g (1mol) of aluminum isopropoxide within 1 hour, react at -10~10℃ for 20 hours; slowly raise the temperature to 10~20℃, stir for 1 hour, filter; then heat to dissolve with 800ml of water, After cooling to 0-10°C, adding hydrochloric acid to acidify to pH 5-7, stirring for 1 hour and filtering; vacuum drying to obtain 183.9g. The yield was 97.2%, and the content detected by HPLC was 96.1%.

[0048] In addition, under the same conditions in Example 2, using sodium methoxide and sodium ethoxide as the condensing agent and aluminum isopropoxide as the condensing agent w...

Example Embodiment

[0049] Example 3 Preparation of 4,6-dihydroxy-5-methyl-2-mercaptopyrimidine (using diethyl 2-methylmalonate as raw material)

[0050] The chemical reaction formula is as follows:

[0051]

[0052] Add 380.7g (5mol) of thiourea and 2000ml of toluene into the reactor, and heat to about 50℃ to dissolve; add 174.2g (1mol) of diethyl 2-methylmalonate, control the temperature at 10-20℃; in 1 hour Add 613g (3mol) of aluminum isopropoxide and react for 15 hours at 10-20°C; filter; then heat to dissolve with 800ml water, cool to 0-10°C, add hydrochloric acid to acidify to pH 5-7, stir for 1 hour and filter; 144.9g was dried. The yield was 91.6%, and the content detected by HPLC was 96.2%.

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Abstract

The invention provides a method for preparing a thiobarbituric acid compound shown as formula I in the specification. In an organic solvent, a malonate diester compound or derivatives thereof, thiourea and aluminum isopropoxide undergo cyclization reaction under certain conditions to obtain the thiobarbituric acid compound (formula I). The method is high in yield, solves the problem of low yield in the prior art, is easy in factory operation, effective and environment-friendly, and is favorable for large-scale production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a method for preparing thiobarbituric acid compounds. Background technique [0002] Dihydroxy-2-mercaptopyrimidine (2-thiobarbituric acid) and its derivatives are important intermediates in organic synthesis and pharmaceuticals, 4,6-dihydroxy-2-mercaptopyrimidine is used in the production of procaine hydrochloride, Procainamide hydrochloride, p-aminomethylbenzoic acid, folic acid, benzocaine, antispasmodic, cephalosporin V, p-aminobenzoyl glutamic acid, Bernier, and production of reactive brilliant red M -8B, Reactive Violet X-2R and light filter, color film coupler, metal surface rust remover, sunscreen, etc. [0003] The document "Synthesis and Structural Characterization of 5-Benzylidene Thiobarbituric Acid" [Journal of Jiangsu Technical Normal University (Natural Science Edition)] discloses the use of diethyl malonate and thiourea in the presence of sodium ethoxide A meth...

Claims

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Application Information

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IPC IPC(8): C07D239/66
CPCC07D239/66
Inventor 陈小舟
Owner CHONGQING HUABANGSHENGKAI PHARM
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