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A kind of preparation method of asymmetric thiourea compound

A technology of amine compounds and thioureas, applied in the direction of drug combination, organic chemistry, non-central analgesics, etc., to achieve the effect of low reaction cost, simple operation and high reaction efficiency

Active Publication Date: 2021-01-15
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported method for the synthesis of asymmetric thiourea compounds requires a two-step reaction, and the two amine compounds need to be added to the reaction system step by step, and the reaction requires a base as a promoter or a reaction under microwave conditions.

Method used

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  • A kind of preparation method of asymmetric thiourea compound
  • A kind of preparation method of asymmetric thiourea compound
  • A kind of preparation method of asymmetric thiourea compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 2-Naphthylamine (0.2mmol), carbon disulfide (0.24mmol), diethylamine (0.24mmol) and DMSO (2.0mL) were respectively added into a 5mL reaction flask, and stirred at 70°C. TLC tracking detection reaction. After 1 hour, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. All organic layers were combined, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (25% ethyl acetate petroleum ether solution) to obtain 49.1 mg of product with a yield of 95%. The reaction process is shown in the following formula:

[0032]

[0033] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0034] 1 H NMR (500MHz, DMSO-d 6 )δ9.15(brs,1H),7.86(t,J=9.1Hz,2H), 7.81(d,J=8.8Hz,1H),7.71(s,1H),7.56–7.54(m,1H), 7.49–7.43(m,2H), 3.79(q,J=6.9Hz,4H),1.21(t,J=7.0Hz,6H)ppm; 13 C NMR (12...

Embodiment 2

[0036]Add 2-naphthylamine (0.2mmol), carbon disulfide (0.24mmol), diethylamine (0.24mmol) and DMF (2.0mL) into a 5mL reaction flask respectively, and stir at 70°C. TLC tracking detection reaction. After 4 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. Combine all organic layers, dry with anhydrous sodium sulfate, concentrate, and separate by column chromatography (25% ethyl acetate petroleum ether solution), obtain product 43.9mg, productive rate is 85%, and reaction process is shown in the following formula:

[0037]

[0038] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0039] 1 H NMR (500MHz, DMSO-d 6 )δ9.15(brs,1H),7.86(t,J=9.1Hz,2H), 7.81(d,J=8.8Hz,1H),7.71(s,1H),7.56–7.54(m,1H), 7.49–7.43(m,2H), 3.79(q,J=6.9Hz,4H),1.21(t,J=7.0Hz,6H)ppm; 13 C NMR (126MHz, DMSO-d 6 )δ179.6...

Embodiment 3

[0041] Add 2-naphthylamine (0.2mmol), carbon disulfide (0.24mmol), diethylamine (0.24mmol) and MeCN (2.0mL) into a 5mL reaction flask respectively, and stir at 70°C. TLC tracking detection reaction. After 12 hours, the reaction was stopped. Water and ethyl acetate were added to the reaction system, the organic layer was separated, and the aqueous layer was washed three times with ethyl acetate. All organic layers were combined, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (25% ethyl acetate petroleum ether solution) to obtain 41.9 mg of product, with a yield of 81%. The reaction process is shown in the following formula:

[0042]

[0043] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares:

[0044] 1 H NMR (500MHz, DMSO-d 6 )δ9.15(brs,1H),7.86(t,J=9.1Hz,2H), 7.81(d,J=8.8Hz,1H),7.71(s,1H),7.56–7.54(m,1H), 7.49–7.43(m,2H), 3.79(q,J=6.9Hz,4H),1.21(t,J=7.0Hz,6H)ppm; 13 C NMR (126MHz, D...

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Abstract

The invention discloses a preparation method of asymmetric thiourea compounds, and the method comprises the following steps: synthesizing the asymmetric thiourea compounds by taking amine compounds and carbon disulfide as substrates in a DMSO or DMF solvent. The method synthesizes the asymmetric thiourea compounds in one step through series reaction of three components. The reaction raw materialsare cheap and easily available, and the preparation method is simple. The reaction requires only the solvent, does not need other additives, has high yield and simple operation, and is suitable for the synthesis of different types of asymmetric thiourea compounds. The method can be used for synthesizing a series of asymmetric thiourea compounds, and the synthesized products can not only be used asintermediate compounds, but also be used for further constructing complex active compounds; at the same time, the compounds have great potential for drug activity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for preparing asymmetric thiourea compounds through series reactions only requiring a solvent. Background technique [0002] Thiourea compounds have received a lot of attention in the field of medicinal chemistry due to their wide range of biological activities. Thiourea derivatives and metal complexes have been shown to have antibacterial, analgesic, anticancer and anti-inflammatory activities. Some thiourea derivatives have been developed into drugs for clinical treatment of diseases, such as hyperthyroidism drugs, sedative hypnotics and so on. Thiourea compounds play a very important role in pesticide chemistry. Many thiourea derivatives have been developed into insecticides, herbicides, rodenticides, fungicides, etc. In the field of synthetic chemistry, thiourea is a very useful substrate for the synthesis of different kinds of important compounds, suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C335/16C07D217/06C07D211/16C07D295/215C07C335/18C07D213/75C07D215/38A61P29/00
CPCA61P29/00C07C335/16C07C335/18C07D211/16C07D213/75C07D215/38C07D217/06C07D295/215
Inventor 宋增强詹玲玲丁超超王绍丽盛耀光梁广
Owner WENZHOU MEDICAL UNIV