Preparation method of 4,5-disubstituted-2-substituted aminothiazole compound

A technology for aminothiazoles and compounds, which is applied in the field of compound synthesis, can solve the problems of harsh reaction conditions, cumbersome operations, and poor applicability of different functional groups, and achieve the effects of mild reaction conditions, less environmental pollution, and easy-to-operate steps

Inactive Publication Date: 2016-04-27
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Although there are many reports on the synthesis of thiazole compounds, the known synthetic methods still have problems such as difficult acquisition of raw materials, harsh reaction conditions, low product yield, difficult post-processing, poor applicability to different functional groups, and cumbersome operations.

Method used

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  • Preparation method of 4,5-disubstituted-2-substituted aminothiazole compound
  • Preparation method of 4,5-disubstituted-2-substituted aminothiazole compound
  • Preparation method of 4,5-disubstituted-2-substituted aminothiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1, 4-methyl-5-phenyl-2-aminothiazole (m1)

[0057] Add 179.1 mg (1 mmol) of 2-methyl-2-nitro-3-phenyloxirane and 152.2 mg (2 mmol) of thiourea into the reaction flask, and then add K 2 CO 3 212.0mg (2mmol), methanol 5.0ml, after the addition was complete, the reaction was stirred at room temperature (25°C) for 6-8 hours, and the reaction was detected by TLC (petroleum ether: ethyl acetate = 20:1 volume ratio). When the TLC detection reaction result is that 2-methyl-2-nitro-3-phenyloxirane disappears, it means that the reaction has ended.

[0058] After the reaction was finished, the solvent was evaporated by a rotary evaporator, 60ml of water was added, extracted three times with 3×20mL ethyl acetate, the organic layer (located on the upper layer) was combined and washed three times with 3×20mL saturated brine, and then washed with anhydrous sodium sulfate ( 2.0 g) was dried for 30 minutes, and concentrated by a rotary evaporator until there was basically n...

Embodiment 2

[0084] Embodiment 2, 4-ethyl-5-phenyl-2-aminothiazole (m2)

[0085] Replace 2-methyl-2-nitro-3-phenyloxirane with 2-ethyl-2-nitro-3-phenyloxirane, the molar weight is constant, and the rest are equal to Example 1 . 180.9 mg of 4-ethyl-5-phenyl-2-aminothiazole was obtained as a white powder, with a yield of 88.7%.

[0086] Its structural formula is:

[0087]

[0088] Whitepowder; mp: 128.3~129.0℃; 1 HNMR (500MHz, CDCl 3 )δ7.41–7.31(m,4H),7.28(dd,J=10.5,3.9Hz,1H),5.12(s,2H),2.62(q,J=7.5Hz,2H),1.25(t,J =7.5Hz,3H). 13 CNMR (126MHz, CDCl 3 )δ165.51(s),149.39(s),132.68(s),129.05(s),128.58(s),126.99(s),120.93(s),77.29(s),77.04(s),76.78( s),22.94(s),14.19(s).HRMS(ESI):m / zcalcdforC 11 h 13 N 2 S[M+H] + :205.0794,found:205.0797.

Embodiment 3

[0089] Example 3, 4-methyl-5-(4-fluoro-phenyl)-2-aminothiazole (m3)

[0090] Replace 2-methyl-2-nitro-3-phenyloxirane with 2-methyl-2-nitro-3-(4-fluoro-phenyl)-oxirane, the molar weight remains unchanged , all the other are with embodiment 1. 199.1 mg of 4-methyl-5-(4-fluoro-phenyl)-2-aminothiazole was obtained as a white powder product, with a yield of 95.7%.

[0091] Its structural formula is:

[0092]

[0093] Whitepowder; mp: 165.5~167.0℃; 1 HNMR (500MHz, CDCl 3 )δ7.35–7.28(m,2H),7.10–7.02(m,2H),5.18(s,2H),2.27–2.25(m,3H). 13 CNMR (126MHz, CDCl 3 ( s),77.30(s),77.04(s),76.79(s),15.85(s).HRMS(ESI):m / zcalcdforC 10 h 10 FN 2 S[M+H] + :209.0543,found:209.0544.

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Abstract

The invention discloses a preparation method of a 4,5-disubstituted-2-substituted aminothiazole compound. The preparation method comprises steps as follows: 1), nitro epoxy compounds and thiourea compounds react at the room temperature for 4-8 h in the presence of a solvent and a basic catalyst; a mole ratio of the nitro epoxy compounds to the thiourea compounds to the basic catalyst is 1: (1.8-2.2): (1.8-2.2); 2), a reaction liquid obtained in the step 1) is concentrated, subjected to solvent removal and added with water, a mixture is extracted by dichloromethane, an organic layer is obtained and then is washed, dried and concentrated by a rotary evaporator; 3), the concentrate obtained in the step 2) is subjected to silica-gel column chromatography, and the 4,5-disubstituted-2-substituted aminothiazole compound is obtained.

Description

technical field [0001] The invention belongs to a compound synthesis method, and mainly relates to a preparation method of a 4,5-disubstituted-2-substituted aminothiazole compound. Background technique [0002] As a class of five-membered heterocyclic compounds with broad-spectrum biological activity, thiazole compounds have important applications in the fields of medicine, pesticides, and materials. Especially in recent years, studies have found that the thiazole ring, as a very important structural unit, widely exists in many natural products and drugs, such as Tiazofurinanddasatinib, Ritonavir, Nizatidine, VitaminB1, Epothilones, Thiostreptonandthiaminepyrophosphate, etc., which are used for tumors, AIDS , Ulcers, allergies, high blood pressure, osteoporosis, asthma and other diseases. [0003] Due to the important application value of thiazole compounds, their synthetic methods have been widely concerned, among which the thiazole synthesis method proposed by Hantzsch et...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/40C07D277/42C07D417/12
CPCC07D277/40C07D277/42C07D417/12
Inventor 章国林赵冬红郭闪闪俞永平
Owner ZHEJIANG UNIV
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