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

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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 ...

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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 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, its structural formula is shown in S-1; soluble in benzene, toluene, etc., almost insoluble in water, is an important fine chemical intermediate, mainly used for the synthesis of antipsychotic drug quetiapine hemifumarate (CAS: 111974-72-2). [0003] [0004] Comprehensive literature reports, the preparation of 2-aminodiphenyl sulfide at present mainly adopts the following methods: [0005] 1. Using o-iodoaniline and thiophenol in CuI as catalyst, K 2 CO 3 As a base, the reaction occurs 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 thiophenol to react under the action of alkali KOH to gen...

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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