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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 isopropoxide react the barbituric acid compound shown in formula I under certain conditions, and yield is high, has overcome There is the problem of low yield in the prior art

Method used

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  • Method for preparing thiobarbituric acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[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 to the reactor, heat to about 50°C to dissolve; add 160.2g (1mol) of diethyl malonate, heat up to 60-70°C; within 1 hour After adding 20.4g (0.1mol) of aluminum isopropoxide, react at 70-80°C for 4 hours; slowly cool to 10-20°C and stir for 1 hour, filter; then heat to dissolve with 800ml of water, cool to 0-10°C, add hydrochloric acid to acidify to The pH was 5-7, stirred for 1 hour and filtered; vacuum-dried to obtain 130.7g. Yield 94.6%, content 98.8%.

Embodiment 2

[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 thiourea 761g (10mol) and isopropanol 2000ml into the reactor, heat to about 50°C to dissolve; add 1-ethyl 3-methyl 2-nitromalonate diester 191.1g (1mol), 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℃ and stir for 1 hour, filter; then heat and dissolve with 800ml of water, After cooling at 0-10°C, add hydrochloric acid to acidify to pH 5-7, stir for 1 hour and filter; vacuum-dry 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 ethylate as the condensing agent and using aluminum isopropoxide as the condensing agent is ...

Embodiment 3

[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 to the reactor, heat to about 50°C to dissolve; add 174.2g (1mol) of diethyl 2-methylmalonate, control the temperature at 10-20°C; Add 613g (3mol) of aluminum isopropoxide internally, react at 10-20°C for 15 hours; filter; then heat and dissolve with 800ml of water, cool down at 0-10°C, add hydrochloric acid to acidify to pH 5-7, stir for 1 hour and filter; vacuum Dry to yield 144.9 g. 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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