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Synthetic method of 4,5-disubstituted-2-aminothiazole compound

The technology of an aminothiazole and a synthesis method, which is applied in the field of compound synthesis, can solve the problems of harsh reaction conditions, high cost, low product yield and the like, and achieves the effects of mild reaction conditions, little environmental pollution, and easy steps to operate.

Inactive Publication Date: 2018-12-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Although there are many reports on the synthesis of 2-aminothiazole compounds, the known synthetic methods still have problems such as difficult acquisition of raw materials, harsh reaction conditions, environmental pollution, high cost, low product yield, and difficult post-processing.

Method used

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  • Synthetic method of 4,5-disubstituted-2-aminothiazole compound
  • Synthetic method of 4,5-disubstituted-2-aminothiazole compound
  • Synthetic method of 4,5-disubstituted-2-aminothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1, 4-methyl-5-phenyl-2-phenylaminothiazole (m1)

[0048] Add 179.1mg (1mmol) of 2-methyl-2-nitro-3-phenyloxirane, 291.5mg (3mmol) of potassium thiocyanate, and 5ml of n-propanol into the reaction flask, and set at room temperature (10~ 25°C) stirring reaction, TLC detection reaction (petroleum ether: ethyl acetate = 20:1 volume ratio), when the TLC detection reaction result is 2-methyl-2-nitro-3-phenyloxirane disappears 279.4mg (3mmol) of aniline was added, and the reaction was stirred at 40±5°C for 18 hours.

[0049] After the reaction was completed, 60ml of water was added, extracted three times with 3×20mL ethyl acetate, and the organic layer (located on the upper layer) was combined and washed three times with 3×20mL saturated brine, then dried with anhydrous sodium sulfate (2.0g) for 30 minutes, When the rotary evaporator is concentrated until there is basically no slip-out liquid, the concentrate is obtained;

[0050] Concentrate column chromatography, w...

Embodiment 2

[0070] Example 2, 4-methyl-5-(4-bromophenyl)-2-phenylaminothiazole (m2)

[0071] Replace 2-methyl-2-nitro-3-phenyloxirane with 2-methyl-2-nitro-3-(4 bromophenyl)-oxirane, the molar weight remains unchanged, and the rest Identical to Example 1. 303.8 mg of 4-methyl-5-(4-bromophenyl)-2-phenylaminothiazole was obtained as light yellow powder, with a yield of 88%.

[0072] Its structural formula is:

[0073]

[0074] Pale yellow powder; 1 H NMR (500MHz, CDCl 3 )δ7.57(s,1H),7.50(d,J=8.5Hz,2H),7.38-7.31(m,4H),7.27(s,1H),7.26(s,1H),7.09(t,J =7.5Hz,1H),2.36(s,3H). 13 CNMR (125MHz, CDCl 3 )δ162.61,144.03,140.10,131.79,131.55,130.28,129.60,123.33,120.83,119.12,118.50,16.29.HRMS(ESI):m / z calcd for C 16 h 14 BrN 2 S[M+H] + :345.0056,found:345.0054.

Embodiment 3

[0075] Example 3, 4-methyl-5-(2-bromophenyl)-2-phenylaminothiazole (m3)

[0076] Replace 2-methyl-2-nitro-3-phenyloxirane with 2-methyl-2-nitro-3-(2-bromophenyl)-oxirane, the molar weight is constant, All the other are with embodiment 1. 262.4 mg of the product 4-methyl-5-(2-bromophenyl)-2-phenylaminothiazole was obtained as light yellow powder, with a yield of 76%.

[0077] Its structural formula is:

[0078]

[0079] Pale yellow powder; 1 H NMR (500MHz, CDCl 3 )δ7.86(s,1H),7.66(d,J=8Hz,1H),7.39-7.32(m,6H),7.221(t,J=7Hz,1H),7.06(t,J=6Hz,1H ),2.15(s,3H). 13 C NMR (125MHz, CDCl 3 )δ163.63,145.66,140.25,133.31,133.13,132.95,129.77,129.53,127.29,125.79,123.08,118.36,15.93.HRMS(ESI):m / z calcd for C 16 h 14 BrN 2 S[M+H] + :345.0056,found:345.0058.

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Abstract

The invention discloses a synthetic method of a 4,5-disubstituted-2-aminothiazole compound. The synthetic method sequentially comprises the following steps: reacting by virtue of nitro epoxy compounds, potassium thiocyanate and amine compounds at 40+ / -5 DEG C in the presence of a solvent, extracting obtained reaction liquid and ethyl acetate, washing and drying an obtained organic layer, and concentrating by virtue of a rotary evaporator; and carrying out silica gel column chromatography on the obtained concentrate, so as to obtain the 4,5-disubstituted-2-aminothiazole compound. The syntheticmethod of the 4,5-disubstituted-2-aminothiazole compound has the technical advantages that the raw materials are easily available, the reaction conditions are mild, the yield is high, the post-treatment is convenient, and the like.

Description

technical field [0001] The synthesis method of the compound of the present invention mainly relates to the synthesis method of 4,5-disubstituted-2-aminothiazole compound. Background technique [0002] Thiazoles are a class of five-membered heterocyclic compounds that are widely distributed and have important biological activities. They are widely used in many fields, especially 2-aminothiazoles, which are widely used in the field of medicine and are used in antibacterial , antifungal, anticancer, antiviral, anti-inflammatory, hypoglycemic, antiepileptic, antiparasitic and other drugs, such as antibiotic drug cefixime, anticancer drug dasatinib, antiparasitic drug nitazoxin Special, anti-inflammatory drug meloxicam, in addition to pesticides, materials, environmental testing and other fields. [0003] Because 2-aminothiazole compounds have important application value, some synthetic methods about it have been reported. The most classic synthesis method is the Hantzsch ring ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/42
Inventor 章国林竺越王其林俞永平
Owner ZHEJIANG UNIV