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Method for preparing acylferrocenyl hydrazinodithio acid ester Schiff base

The technology of acyl ferrocenyl hydrazino dithioate and acyl ferrocenyl hydrazino dithioformate is applied in the field of preparing acyl ferrocenyl hydrazino dithioate Schiff base, which can solve the problem of liquid The phase method has long reaction time, organic solvent pollutes the environment, catalyst cannot be recycled and other problems, and achieves the effect of high yield, short reaction time and high efficiency

Inactive Publication Date: 2019-07-05
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst used in the solid-phase method cannot be recycled, the reaction time of the liquid-phase method is long, and the environment is polluted by organic solvents.

Method used

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  • Method for preparing acylferrocenyl hydrazinodithio acid ester Schiff base
  • Method for preparing acylferrocenyl hydrazinodithio acid ester Schiff base
  • Method for preparing acylferrocenyl hydrazinodithio acid ester Schiff base

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Preparation of N'-ferrocene methylene-hydrazino dithioformate methyl ester:

[0025]

[0026] In the first step, 1 mol of choline chloride and 2 mol of methanesulfonic acid are added to the reaction vessel, and stirred at 80°C until fully dissolved to obtain a eutectic solvent;

[0027] In the second step, after cooling the reaction system to room temperature, add 1 mol of formyl ferrocene and 1 mol of methyl hydrazinodithioformate, slowly raise the temperature to 80°C, and monitor by TLC until the reaction is complete;

[0028] In the third step, the reaction liquid was cooled to room temperature, and solids were separated out, filtered with suction, and the solids were washed with a small amount of water to obtain the product with a yield of 91.2%, m.p. 145-147°C; the filtrate was recovered to obtain a eutectic solvent.

[0029] The structural characterization data of the product are:

[0030] IR(KBr)v:3122(v- NH- ), 3079 (v Unsaturated C-H ), 2963 (v Saturated C-H ...

Embodiment 2

[0032] Example 2 Preparation of N′-ferrocene methylene-hydrazinodithiocarbamate ethyl ester:

[0033]

[0034] In the first step, add 1 mol of choline chloride and 2 mol of methanesulfonic acid to the reaction vessel, and stir at 80°C until fully dissolved to obtain a eutectic solvent;

[0035] In the second step, after cooling the reaction system to room temperature, add 1 mol of formyl ferrocene and 1 mol of methyl hydrazinodithioformate, slowly increase the temperature to 80°C, and monitor by TLC until the reaction is complete;

[0036] In the third step, the reaction solution was cooled to room temperature, and solids were separated out, filtered with suction, and the solids were washed with a small amount of water to obtain the product with a yield of 93.1%, m.p. 126-128°C; the filtrate was recovered to obtain a eutectic solvent.

[0037] The structural characterization data of the product are:

[0038] IR(KBr)v:3115(v- NH- ), 2927(v Saturated C-H ), 1599(v- C=N ),1388(v- CH3 ),...

Embodiment 3

[0040] Example 3 Preparation of N′-ferrocene methylene-hydrazinodithiocarbamate benzyl ester:

[0041]

[0042] In the first step, add 1 mol of choline chloride and 2 mol of methanesulfonic acid to the reaction vessel, and stir at 80°C until fully dissolved to obtain a eutectic solvent;

[0043] In the second step, after cooling the reaction system to room temperature, add 1 mol of formyl ferrocene and 1 mol of methyl hydrazinodithioformate, slowly increase the temperature to 80°C, and monitor by TLC until the reaction is complete;

[0044] In the third step, the reaction solution was cooled to room temperature, and solids were separated out, filtered with suction, and the solids were washed with a small amount of water to obtain the product with a yield of 93.1%, m.p. 189-192°C; the filtrate was recovered to obtain a eutectic solvent.

[0045] The structural characterization data of the product are:

[0046] IR(KBr)v:3174(v- NH- ), 3084 (v Unsaturated C-H ), 2901(v Saturated C-H ),15...

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Abstract

The invention discloses a method for preparing an acylferrocenyl hydrazinodithio acid ester Schiff base. The method comprises the following steps: adding formula amounts of choline chloride (A mol) and methanesulfonic acid (B mol) into a reaction vessel, and performing stirring at 80 DEG C until complete dissolving in order to obtain a eutectic solvent; adding formula amounts of acylferrocene (C mol) and hydrazinodithio acid ester (D mol), slowly heating the obtained solution to 80 DEG C, performing TLC monitoring until a reaction is finished (1 h), cooling the obtained reaction solution to room temperature to precipitate a solid, carrying out suction filtration, washing the solid with a small amount of water, and drying the washed solid to obtain the product with a yield of 90% or more; and recovering the obtained filtrate to obtain the eutectic solvent, wherein a ratio of A:B:C:D is 1:(1-4):(1-1.5):(1-1.5). The method has the advantages of short reaction time, high efficiency, high yield, high purity of the product, recyclable catalyst, greenness, environmental protection and cost reduction.

Description

Technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a method for preparing Schiff base of acyl ferrocene hydrazino dithioester. Background technique [0002] The existing methods for preparing Schiff base of acylferrocene hydrazino dithioester generally include solid phase method and liquid phase method. The solid phase method uses p-toluenesulfonic acid as a catalyst, and the liquid phase method uses reflux in ethanol. The catalyst used in the solid phase method cannot be recycled, the liquid phase method takes a long time to react, and it pollutes the environment with organic solvents. Summary of the invention [0003] The purpose of the present invention is to provide a method for preparing acylferrocene hydrazino dithioester Schiff base, which can prepare acylferrocene hydrazino dithioester Schiff base with high yield and high purity. [0004] In order to achieve the above objectives, the present invention ado...

Claims

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Application Information

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IPC IPC(8): C07F17/02
CPCC07F17/02Y02P20/584
Inventor 刘玉婷邹倩尹大伟杨岚党阳李洁孙嘉希
Owner SHAANXI UNIV OF SCI & TECH
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