Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole

A technology of acyl ferrocene and acetyl ferrocene, applied in chemical instruments and methods, metallocene, organic chemistry, etc., can solve the problems of difficult to achieve mass production, complicated post-processing process, and high reaction temperature, and achieve the effect Good, short response time, simple operation effect

Inactive Publication Date: 2015-04-29
SHAANXI UNIV OF SCI & TECH
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0003] The acyl ferrocenyl 2-amino-5-substituted-1,3,4-thiadiazoles prepared in the prior art mostly adopt the liquid phase reflux synthesis method, although the product is successfully synthesized, but its reaction temperature is relatively high , takes a long time, the post-processing process is complicated, it is difficult to achieve mass production in industrial production, and the synthesis process needs to be further improved

Method used

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  • Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole
  • Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole
  • Method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] 1) Add 0.001mol ferroceneformaldehyde, 0.001mol 2-amino-5-methyl-1,3,4-thiadiazole and 0.0012mol p-toluenesulfonic acid to a dry mortar, and grind at room temperature until the raw materials react complete (reaction monitored by TLC), the time is 15 min, and then it is kept in an oven at 50° C. for 30 min.

[0034] 2) Then cool it down to room temperature and add absolute ethanol, filter the mixture with suction to remove the catalyst p-toluenesulfonic acid, and concentrate the filtrate to dryness under reduced pressure to obtain the crude product. The crude product is recrystallized with absolute ethanol to obtain formyl ferrocene 2-amino-5-methyl-1,3,4-thiadiazole.

[0035] IR (KBr, v / cm -1 ): 3555, 3473, 2960, 2933, 1618, 1455, 1378, 1377, 1196, 1196, 1074, 669, 479;

[0036] 1 H-NMR: 4.820 (m, 2H, replace the H on the ortho position of C=N on the alocene ring); 4.752 (m, 2H, replace the H on the alocene ring and the C=N meta-position); 2.505 (vs, 6H, DMSO-d б s...

Embodiment 2

[0038] 1) Add 0.001mol acetylferrocene, 0.001mol 2-amino-1,3,4-thiadiazole and 0.0012mol p-toluenesulfonic acid to a dry mortar, and grind at room temperature until the reaction of the raw materials is complete (monitored by TLC reaction), the time is 20min, and then it is kept in an oven at 50°C for 30min.

[0039] 2) Then cool it down to room temperature and add absolute ethanol, filter the mixture with suction to remove the catalyst p-toluenesulfonic acid, and concentrate the filtrate to dryness under reduced pressure to obtain the crude product. The crude product is recrystallized with absolute ethanol to obtain 2-amino-1,3,4-thiadiazole acetyl ferrocene.

[0040] Depend on figure 1 Visible, 3301, 3089cm -1 It is the strong absorption peak of C-H stretching vibration on ferrocene; 1504, 1423cm -1 It is the strong peak of C=N stretching vibration absorption; 825cm -1 It is the C-H stretching vibration absorption weak peak on ferrocene; 490cm -1 Absorb weak peaks for N-...

Embodiment 3

[0043] 1) Add 0.001mol acetylferrocene, 0.001mol 2-amino-5-methyl-1,3,4-thiadiazole and 0.0012mol p-toluenesulfonic acid to a dry mortar, and grind at room temperature until the raw material The reaction was complete (monitored by TLC) for 25 minutes, and then kept in an oven at 50° C. for 30 minutes.

[0044] 2) Then cool it down to room temperature and add absolute ethanol, filter the mixture with suction to remove the catalyst p-toluenesulfonic acid, and concentrate the filtrate to dryness under reduced pressure to obtain the crude product. The crude product is recrystallized with absolute ethanol to obtain acetyl ferrocene 2-amino-5-methyl-1,3,4-thiadiazole.

[0045] IR (KBr, v / cm -1 ): 3426, 2925, 1605, 1527, 1427, 1377, 1104, 1001, 828, 648, 495;

[0046] 1 H-NMR: 4.53-4.80 (2H, Fc-H, multiplet), 4.26 (5H, Fc-H, triplet), 2.05-2.52 (3H, -CH 3 ,Unimodal).

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Abstract

The invention discloses a method for preparing carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole. The method comprises the following steps: adding A mol of carbonyl ferrocene, B mol of 2-amino-5-substituted-1,3,4-thiadiazole and C mol of p-toluenesulfonic acid into a dried mortar, grinding at room temperature until the raw material reaction (a TLC monitoring reaction) is complete, preserving the temperature in a drying box under the condition of 50 DEG C for 30 minutes, cooling to room temperature, adding absolute ethyl alcohol, performing suction filtration on the mixed solution, removing the catalyst p-toluenesulfonic acid, performing vacuum concentration until the filtrate is dried, thereby obtaining the crude product, wherein the ratio of A to B to C is 1:(1.0-1.2):(1.0-1.2); and recrystallizing the crude product by using absolute ethyl alcohol, thereby obtaining the purified product. The method disclosed by the invention is short in reaction time, mild in reaction conditions, low in equipment requirements, easy to operate and simple in after-treatment and is a green, economic, environment-friendly and high-efficiency method for synthesizing the carbonyl ferrocene condensed 2-amino-5-substituted-1,3,4-thiadiazole, a solvent is not needed, the catalyst can be repeatedly used, and the yield is over 85 percent.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a method for preparing acyl ferrocene 2-amino-5-substituted-1,3,4-thiadiazole. Background technique [0002] 1,3,4-Thiadiazoles are important heterocyclic compounds containing N, C, and S heteroatoms. They are similar to aromatic rings and have aromaticity and conjugation effects. Its substituted aryl group can be used as an active group to react chemically with various compounds, so thiadiazole compounds whose substituent is an active group are often used as active intermediates in organic synthesis. In medicine, it has anti-cancer, anti-HIV, anti-virus and anti-fungal properties. In terms of pesticides, it has the functions of insecticide, antibacterial, weed control and plant growth regulation. Acyl ferrocene has a sandwich structure and has special aroma, lipophilicity, low toxicity, and biological activity. Ferrocene-containing drugs have been used in the fields of treati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 刘玉婷杨阿宁尹大伟吕博黄涛吴倩倩王雨薇许娟娟
Owner SHAANXI UNIV OF SCI & TECH
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