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Preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide

A technology of n-butyraldehyde bisthiosemicarbazide and phthalimide, which is applied in the direction of organic chemistry, can solve the problems of difficult filtration, cumbersome operation, and long reaction route, so as to improve efficiency, reduce operating cost, and facilitate operation Effect

Inactive Publication Date: 2019-07-09
HUAIBEI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The reaction route of this method is long, and the operation is more loaded down with trivial details
Especially iron powder reduction nitro group reaction, compound VI and compound VII mixed in iron powder is not easy to achieve complete reaction, after the reaction, because the iron powder is too fine, it is difficult to filter, so it is not suitable for industrial production

Method used

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  • Preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide
  • Preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide
  • Preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide

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Experimental program
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Embodiment 1

[0039] Embodiment 1: preparation compound II

[0040] Take N-ethoxycarbonylphthalimide (21.9g, 0.1mol), sodium carbonate (10.6g, 0.1mol) and 100mL water in a 250mL single-necked bottle, add dropwise alanine (8.9g, 0.1mol ) in 30 mL aqueous solution, stirred at room temperature for 2 h, added dropwise 2M hydrochloric acid to adjust the pH value to 2-3, filtered and dried to obtain 18 g of compound II. Yield 82%.

[0041] 1 HNMRδ1.71(s,3H),5.02(q,1H),7.69-7.75(m,2H),7.82-7.88(m,2H).MS(ESI)m / z 218.2[M-H] -

[0042] Table 1: Screening of Reaction Conditions for Preparation of Compound II

[0043]

Embodiment 2

[0044] Embodiment 2: preparation compound II

[0045] Take N-ethoxycarbonylphthalimide (21.9g, 0.1mol), sodium carbonate (10.6g, 0.1mol) and 100mL water in a 250mL single-necked bottle, add alanine (8.9 g, 0.1mol) in 30mL aqueous solution, after dripping, naturally rise to room temperature and stir for 2h, add dropwise 2M hydrochloric acid to adjust the pH value to 2-3, filter and dry to obtain 17g of compound II with a yield of 78%.

Embodiment 3

[0046] Embodiment 3: preparation compound II

[0047] Take N-ethoxycarbonylphthalimide (21.9g, 0.1mol), sodium carbonate (12.7g, 0.12mol) and 100mL water in a 250mL single-necked bottle, add alanine (8.9g, 0.1mol) dropwise ) in 30 mL aqueous solution, stirred at room temperature for 2 h, added dropwise 2M hydrochloric acid to adjust the pH value to 2-3, filtered and dried to obtain 17.5 g of compound II with a yield of 80%.

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Abstract

The invention relates to a preparation method of 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide (I). The preparation method comprises the steps: adopting alanine and N-ethoxycarbonyl phthalimide as a starting material, and performing aminoacylation, methyl-lithium addition, an oxidation reaction and a condensation reaction so as to obtain the target product 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide (I). The method for synthesizing 3-phthalimide-2-oxy-n-butyraldehyde thiosemicarbazide has the advantages of few reaction steps, simple operation, suitability for large-scale production and the like.

Description

technical field [0001] The technical field of preparation of pharmaceutical products of the present invention, in particular relates to a preparation method of 3-phthalimide-2-oxo-n-butyraldehyde bisthiosemicarbazide. Background technique [0002] 3-phthalimide-2-oxo-n-butyraldehyde bisthiosemicarbazide (as shown in formula I), also known as phthalobutanol or luciferin, is a thiosemicarbazone antiviral drug. It has anti-Chlamydia trachomatis and anti-herpes virus activity, and its inhibitory effect on Chlamydia trachomatis is 10 times stronger than aureomycin, and can prevent the reproduction of Chlamydia trachomatis and the formation of inclusion bodies. For herpes zoster, herpes simplex, condyloma acuminatum, superficial fungal infection and various trachoma, etc. Its mechanism of action is mainly to inhibit viral DNA and early protein synthesis. After entering the virus-infected cells, phthalide competes with deoxynucleosides for viral thymidine kinase or cellular kinas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 张顺吉
Owner HUAIBEI NORMAL UNIVERSITY
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