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The preparation method of 4,5-disubstituted-2-aminothiazole compound

An aminothiazole and compound technology, which is applied in the field of compound synthesis, can solve the problems of difficult availability of raw materials, low product yield, environmental pollution and the like, and achieves the effects of novel structure, high reactivity and little environmental pollution

Inactive Publication Date: 2018-09-25
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0014] Although there are many reports on the synthesis of 2-aminothiazole compounds, the known synthetic methods still have problems such as difficult access to raw materials, low product yields, cumbersome operations, and environmental pollution.

Method used

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  • The preparation method of 4,5-disubstituted-2-aminothiazole compound
  • The preparation method of 4,5-disubstituted-2-aminothiazole compound
  • The preparation method of 4,5-disubstituted-2-aminothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0052] Example 1-1, 4-methyl-5-(4-bromophenyl)-2-aminothiazole (m1)

[0053] Add 210.1 mg (2.5 mmol) of 50% cyanamide aqueous solution and 480.4 mg (1 mmol) of sodium sulfide nonahydrate to the reaction flask, then add 2.0 mL of n-propanol, 2-methyl-2-nitro-3-( 128.5 mg (0.5 mmol) of 4-bromophenyl)oxirane. After the addition, the reaction was stirred at room temperature for 8 hours, and the reaction was detected by TLC (dichloromethane: methanol = 20:1 by volume). At this time, the reaction result detected by TLC was that 2-methyl-2-nitro-3-(4-bromophenyl)oxirane disappeared, indicating that the reaction had ended.

[0054] After the reaction is complete, concentrate to remove n-propanol, cool to room temperature, add 60 mL of water, extract the reaction solution with 3×20 mL of ethyl acetate three times, combine the organic layers (on the upper layer) and wash three times with 3×30 mL of saturated brine, then use Drying with anhydrous sodium sulfate (2.0g) for 30 minutes, and con...

Embodiment 1

[0062] Example 1-2: The sodium sulfide nonahydrate is changed to sodium hydrosulfide, the molar amount remains unchanged; the rest is the same as in Example 1. 73.7 mg of 4-methyl-5-(4-bromophenyl)-2-aminothiazole was obtained as a white solid product with a yield of 55%.

Embodiment 1-3

[0063] In Example 1-3, methanol was used instead of n-propanol, and the volume was unchanged; the rest were the same as in Example 1. 96.5 mg of 4-methyl-5-(4-bromophenyl)-2-aminothiazole was obtained as a white solid product with a yield of 72%.

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Abstract

The invention discloses a preparation method of a 4, 5-disubstituted-2-aminothiazole compound. The preparation method sequentially includes following steps: 1), reacting a nitro epoxy compound, a hydrogen cyanamide water solution of 50% in mass concentration and sulfide in a solvent at room temperature; 2), concentrating reaction liquid obtained in the step 1) to remove the solvent, cooling to room temperature, using water and ethyl acetate to extract, and subjecting an obtained organic layer to washing, drying and concentrating by a rotary evaporator; 3), performing silica gel column chromatography on concentrate obtained in the step 2) to obtain the 4, 5-disubstituted-2-aminothiazole compound. A method which is simple and easy to implement is provided for efficiently synthesizing the 4, 5-disubstituted-2-aminothiazole compound.

Description

Technical field [0001] The synthesis method of the compound of the present invention mainly relates to the preparation method of 4,5-disubstituted-2-aminothiazole compound. Background technique [0002] Thiazole compounds are an important class of heterocyclic compounds, which play an important role in pharmaceutical research. In particular, 2-aminothiazole compounds have a wide range of applications in drug discovery and development, such as the synthesis of anti-cancer, anti-tumor, antibacterial, and anti-inflammatory drugs. [0003] Due to the wide application of the 2-aminothiazole group, its synthesis method has been receiving extensive attention. The main synthetic method is the Hantzsch ring condensation method (Hantzsch, A.; Weber, JH Chemische Berichte. 1887, 20, 3118), which uses α-haloketone / aldehyde or α-p-toluenesulfonyl ketone / aldehyde and Thiourea is used as a raw material, and 2-aminothiazole compound (Formula 1) is obtained by condensation. [0004] [0005] Formu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/40
CPCC07D277/40
Inventor 章国林郭闪闪俞永平
Owner ZHEJIANG UNIV
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