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Method for synthesizing monoalkyl oxalate-[(aryl)methenyl]hydrazide compound

A technology of oxalic acid monoalkyl hydrazide and oxalic acid monoalkyl ester, which is applied in the directions of organic chemistry, hydrazone preparation, etc., can solve the problems of many by-products, waste of raw material dialkyl oxalate, etc., and achieves short reaction time and shortening Response time, cost saving effect

Inactive Publication Date: 2018-06-01
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The molar ratio of dialkyl oxalate and hydrazine hydrate used in this document is 3:1, and the dropping temperature and reaction temperature of hydrazine hydrate are both at room temperature. This method has many by-products, and the waste of raw material dialkyl oxalate is too much

Method used

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  • Method for synthesizing monoalkyl oxalate-[(aryl)methenyl]hydrazide compound
  • Method for synthesizing monoalkyl oxalate-[(aryl)methenyl]hydrazide compound
  • Method for synthesizing monoalkyl oxalate-[(aryl)methenyl]hydrazide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Preparation of monoethyl oxalate-[(4-diethylamino-2-hydroxyphenyl)methenyl]hydrazide

[0025]

[0026] Weigh 120mg (0.62mmol) of 4,4-diethylamino salicylaldehyde and monoethyl oxalyl chloride into 10ml aqueous solution of monoethyl oxalate hydrazide, stir at 60°C for 5h, collect the solid by suction filtration, wash with 30ml water The filter cake was vacuum-dried to obtain 170 mg of yellow solid powder, and the calculated yield was 94% relative to 4,4 diethylamino salicylaldehyde.

[0027] 1 H NMR (501MHz, Chloroform-d) δ10.99(s, 1H), 10.17(s, 1H), 8.39(s, 1H), 7.11(d, J=8.5Hz, 1H), 6.32(d, J= 10.2Hz, 2H), 4.48(q, J=7.1Hz, 2H), 3.47(q, J=6.9Hz, 4H), 1.49(t, J=7.1Hz, 3H), 1.28(t, J=7.0Hz ,6H). 13 C NMR (126MHz, Chloroform-d) δ160.86, 154.19, 151.87, 132.90, 106.01, 103.88, 98.12, 63.15, 44.49, 13.96, 12.62.

Embodiment 2

[0029] Preparation of monoethyl oxalate-[(2-methylphenyl)methenyl]hydrazide

[0030]

[0031] Accurately weigh 110 mg (0.917 mmol) of 4-nitro-3-hydroxybenzaldehyde and add it to 10 ml of an aqueous solution of ethyl oxalate hydrazide, stir for 70 min at room temperature, collect the solid by suction filtration, wash the solid three times with 30 ml of water, Vacuum-dried to obtain 150 mg of white powder solid, with a calculated yield of 76.9% relative to 4-nitro-3-hydroxybenzaldehyde.

[0032] 1 H NMR (501MHz, Chloroform-d) δ10.41(s,1H),8.68(s,1H),7.96(s,1H),7.29(d,J=8.2Hz,1H),7.22–7.15(m, 2H), 4.39(q, J=7.1Hz, 2H), 2.46(s, 3H), 1.39(t, J=7.1Hz, 3H). 13 C NMR (126MHz, Chloroform-d) δ160.37, 152.63, 150.34, 137.76, 131.08, 130.93, 130.84, 127.31, 126.36, 63.55, 19.40, 13.97.

Embodiment 3

[0034] Preparation of monoethyl oxalate-[(3,4,5-trimethoxyphenyl)methenyl]hydrazide

[0035]

[0036] Accurately weigh 100 mg (0.5 mmol) of 3,4,5-trimethoxybenzaldehyde and 67 mg (0.5 mmol) of ethyl oxalyl chloride into 10 ml of water, stir at room temperature for 15 min, filter, and wash the filter cake with water several times. Vacuum-dried to obtain 158 mg of a white solid, with a calculated yield of 73.3% relative to 3,4,5-trimethoxybenzaldehyde.

[0037] 1 H NMR (501MHz, Chloroform-d) δ10.82(s, 1H), 8.39(s, 1H), 7.03(s, 2H), 4.44(q, J=7.1Hz, 2H), 3.93(d, J= 6.4Hz, 9H), 1.45(t, J=7.1Hz, 3H). 13 C NMR (126 MHz, Chloroform-d) δ 160.19, 153.43, 151.80, 140.66, 105.15, 63.55, 60.92, 56.26, 13.93.

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Abstract

The invention discloses a method for synthesizing a monoalkyl oxalate-[(aryl)methenyl]hydrazide compound. The method comprises the following steps: the first step: reacting dialkyl oxalate with hydrazine hydrate to obtain monoalkyl oxalate hydrazide; the second step: reacting the obtained monoalkyl oxalate hydrazide with different benzaldehyde derivatives to obtain the corresponding structure monoalkyl oxalate-[(aryl)methenyl]hydrazide compound. Different from conventional synthesis of such compounds using organic solvents, the method for synthesizing the monoalkyl oxalate-[(aryl)methenyl]hydrazide compound uses water as a solvent, has a green and economical character, and has a high conversion rate, a high yield, a fast reaction speed, and simple post-treatment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for synthesizing monoalkyl oxalate-[(aryl)methenyl]hydrazide compounds. Background technique [0002] The Schiff base containing the structure -CO-NH-N=C- has a wide range of application values ​​because of its special structure, which can form stable Schiff base metal complexes with transition metals. Some Schiff base metal complexes have biological activities such as sterilization, anti-tumor, and anti-tuberculosis in the field of medicine; they also have many applications in materials. For example, some heterocyclic Schiff bases show good fluorescence. Materials, photochromic materials, etc. have a wide range of applications; in addition, some complexes formed by Schiff bases and metal Ni can be used as catalysts. The different structures of Schiff base metal complexes determine their different application values, and the diversity of ligands determines the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C249/16C07C251/86
CPCC07C249/16C07C251/86
Inventor 程利平赵志祥庞婉刘洋洋
Owner SHANGHAI INST OF TECH