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Method for realizing green synthesis of asymmetric thiocarbamide

A green synthesis and asymmetric technology, applied in organic chemistry methods, chemical instruments and methods, and the formation/introduction of functional groups, etc., can solve the problems of unsafe production, method limitations, rare raw materials, etc., and achieve convenient separation and purification, high yield Green environmental protection, the effect of easy availability of reaction raw materials

Active Publication Date: 2013-12-11
枣庄市新星钢结构有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The present invention overcomes the limitations of methods in the prior art for synthesizing asymmetric thiourea derivatives using amines as raw materials, rare raw materials, high toxicity, and unsafe production, and provides a green, efficient, and widely applicable synthetic asymmetric thiourea derivative. Thiourea method

Method used

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  • Method for realizing green synthesis of asymmetric thiocarbamide
  • Method for realizing green synthesis of asymmetric thiocarbamide
  • Method for realizing green synthesis of asymmetric thiocarbamide

Examples

Experimental program
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Embodiment 1

[0019] Step 1: Add phenoxythioacyl chloride (1mmol, 0.17g), 15mL of water and aniline (2mmol, 0.19g) sequentially into a 50mL one-necked flask, stir at 25°C for 1h, and stop the reaction. After suction filtration, the filter cake was washed successively with 10% hydrochloric acid and water to obtain a pure N-phenyl-O-phenylthioamide intermediate with a yield of 95.4%.

[0020] Step 2: Add N-phenyl-O-phenylthioamide (1mmol, 0.23g), 15mL of water and benzylamine (1mmol, 0.11g) sequentially into a 50mL single-necked flask, and stir at 100°C for 60min. Stop responding. After cooling and standing, suction filtration, the filter cake was washed successively with 10% hydrochloric acid and water to obtain phenylbenzylthiourea with a yield of 90.2%.

[0021] 1 HNMR(300MHZ,DMSO):δ=9.67(s,1H,NH),8.21(s,1H,NH),7.44(d,J=7.5Hz,2H,ArH),7.34-7.22(m,7H,ArH ),7.11(d,J=7.5Hz,1H,ArH),4.74(d,J=5.7Hz,2H,CH 2 ); 13 CNMR(75MHZ,DMSO):δ=181.2,139.7,139.5,129.1,128.7,127.9,127.3,124.7,123.8,47.6; M...

Embodiment 2

[0023] With reference to the method of Example 1, p-fluorophenoxysulfuryl chloride was used as the carbon sulfide reagent in the first step reaction, and the yield of the N-phenyl-O-phenylthioamide intermediate was 89.6%.

Embodiment 3

[0025] Referring to the method of Example 1, the molar ratio of phenoxythioacyl chloride and aniline in the first step reaction is 1:1, and the yield of N-phenyl-O-phenylthioamide intermediate is 85.3%.

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Abstract

The invention provides a method for realizing green synthesis of asymmetric thiocarbamide, and relates to the field of organic chemical engineering. The method comprises the following steps: (1) synthesizing an O-aryl thioamide intermediate compound by using phenoxy sulfuryl chloride or substituted phenoxy sulfuryl chloride and primary amine as raw materials, wherein the mol ratio of the primary amine to the substituted phenoxy sulfuryl chloride is (1-3):1, water is used as solvent, the reaction temperature is 10-60 DEG C, and the reaction time is 0.5-12 hours; and (2) reacting the O-aryl thioamide intermediate compound with another primary amine to prepare the asymmetric thiocarbamide, wherein the mol ratio of the primary amine to the O-aryl thioamide intermediate compound is (1-3):1, water is used as solvent, the reaction temperature is 65-100 DEG C, and the reaction time is 10-120 minutes. The method provided by the invention has the multiple advantages of accessible reaction raw materials, low toxicity, mild reaction conditions, short reaction time, convenient separation and purification process, wide substrate application range and the like, and has high application value.

Description

technical field [0001] The invention relates to the field of organic chemical industry, in particular to a green method for synthesizing asymmetric thiourea. Background technique [0002] Thiourea is often used to construct heterocyclic skeletons. It is a kind of organic synthesis intermediates and pharmaceutical intermediates with a wide range of uses. It is widely used in medicine, pesticides, dyes, chiral synthesis, clinical medicine, environmental monitoring and biological metabolism, and chemical production. Various fields, therefore, the research on the synthesis method of thiourea has always been an important topic in organic chemistry. [0003] It is a relatively simple and economical method to synthesize thiourea from amines. The common method is to prepare thiourea by one-step condensation of thiophosgene or carbon disulfide and amine compounds, but these two methods have great disadvantages: on the one hand, thiophosgene or carbon disulfide are relatively toxic, ...

Claims

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Application Information

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IPC IPC(8): C07B45/00C07C335/16C07C335/18C07C335/14C07D307/52C07D333/20C07D409/12
Inventor 李正义石嵩孙小强陈新
Owner 枣庄市新星钢结构有限公司
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