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Preparation method of 2-aminophenyl phenyl sulfide

A technology of aminodiphenyl sulfide and diaminodiphenyl sulfide, which is applied in the field of synthesis of 2-aminodiphenyl sulfide, can solve the problems of strong thiophenol odor, environmental pollution, and high price of starting materials, and achieve low cost , easy to obtain raw materials and low cost

Active Publication Date: 2012-07-25
江西扬帆新材料有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] It can be seen that the essence of the above three processes is to form 2-aminodiphenyl sulfide after condensation reaction of halogenated benzene and thiophenol to remove a molecule of hydrogen halide. Due to the high price of starting materials, 2-aminodiphenylsulfide The production cost of phenylene sulfide is relatively high
In addition, the raw material thiophenol is a substance with a strong odor and pollutes the environment

Method used

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  • Preparation method of 2-aminophenyl phenyl sulfide
  • Preparation method of 2-aminophenyl phenyl sulfide
  • Preparation method of 2-aminophenyl phenyl sulfide

Examples

Experimental program
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Embodiment 1

[0043] Embodiment 1, a kind of preparation method of 2-amino diphenyl sulfide, take o-nitroaniline, hydrochloric acid, sodium nitrite, sodium sulfide, acetic anhydride, ethanol, sodium hydroxide etc. as raw materials, carry out the following steps successively:

[0044] Step 1), prepare diazonium salt:

[0045] 13.8g (0.1mol) of o-nitroaniline, 73g of hydrochloric acid solution (11g, 0.3mol) with a mass solubility of 15% were put into a 250ml flask, cooled to 5°C, and 30ml of aqueous sodium nitrite ( 7.9 g, 0.115 mol), adjust the dropping rate to keep the reaction temperature at 5-10 °C, drop after 2 h, continue to stir at 5 °C for 30 min after the dropping is completed, and stop the reaction.

[0046] Step 2), prepare 2,2'-diaminodiphenyl sulfide:

[0047] 150ml of Na with a mass concentration of 17.5% 2S solution (0.4mol) and 12g (0.3mol) NaOH were put into a 500ml flask, heated to 45°C, and all the diazonium salt solutions obtained in step 1) were added dropwise with stir...

Embodiment 2～10

[0053] Change the following reaction conditions in steps 1) to 4) of Example 1:

[0054] In step 1), the diazotization reaction temperature (abbreviated as T 1 ), the mol ratio of o-nitroaniline and sodium nitrite in step 1) (referred to as R 1 ), step 2) in the thioetherification reaction temperature (referred to as T 2 ), the mol ratio of o-nitroaniline and sodium sulfide in step 2) (referred to as R 2 ), step 3) in acylation reaction reagent (referred to as S 1 ), step 4) in the denitrification reaction temperature (referred to as T 3 ), step 4) in the denitrification reaction reagent (referred to as S 2 ) to obtain Examples 2 to 10, and the molar ratios between the remaining reaction raw materials are the same as those of Example 1; thereby obtaining the yield of the corresponding 2-aminodiphenyl sulfide (referred to as Y). The specific content and data results are shown in Table 1.

[0055] Table 1

[0056]

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Abstract

The invention discloses a preparation method of 2-aminophenyl phenyl sulfide. In the method, a diazo reaction, a thioetherfication-reduction 'one pot process' reaction, a salting reaction, an acylation reaction, a single diazo reaction, a denitriding reaction and a neutralizing reaction are performed in sequence on ortho-nitroaniline serving as a raw material, so that 2-aminophenyl phenyl sulfide is obtained. The method comprises the following steps of: firstly, undergoing a diazo reaction with sodium nitrite and hydrochloric acid, undergoing a thioetherfication-reduction 'one pot process' reaction, i.e., thioetherfication reaction with sodium sulfide, raising the temperature, and undergoing a reduction reaction; secondly, reacting with an equal molar amount of hydrochloric acid for salting, reacting with an acylation reagent to form acylamide, and undergoing a diazo reaction with sodium nitrite and hydrochloric acid; and lastly, undergoing a denitriding reaction under the action of a reducing agent (a denitriding reaction reagent), and neutralizing with an alkaline solution to obtain 2-aminophenyl phenyl sulfide. The method disclosed by the invention for preparing the 2-aminophenyl phenyl sulfide has the characteristic of low cost.

Description

Technical field [0001] The present invention relates to a method for synthesizing organic compounds, in particular to a method for synthesizing 2-Amino diphenylsulfide. Background technique [0002] 2-Aminodiphenyl sulfide, its molecular formula is C 12 H 11 NS, whose structural formula is shown as S-1; is soluble in benzene, toluene, etc., and is almost insoluble in water. It is an important fine chemical intermediate and is mainly used in the synthesis of the antipsychotic drug quetiapine hemifumarate (CAS: 111974-72-2). [0003] [0004] According to comprehensive literature reports, the following methods are currently used to prepare 2-aminodiphenyl sulfide: [0005] 1. Use o-iodoaniline and thiophenol in CuI as catalyst, K 2 CO 3 The reaction occurs under the conditions of a base to generate 2-aminodiphenyl sulfide, and the reaction formula is shown in S-2 (Journal of Organic Chemistry, 73(14): 5625-5628, 2008); [0006] 2. Use o-chloronitrobenzene and thiophen...

Claims

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Application Information

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IPC IPC(8): C07C323/37C07C319/20
Inventor 吕雪皓陶明李桂芹钱超张华陈新志
Owner 江西扬帆新材料有限公司
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