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Preparation method of polysubstituted 2-imino thiazole compound

An iminothiazole and multi-substitution technology, which is applied in the field of preparation of multi-substituted 2-iminothiazole compounds, can solve the problems of unrealistic industrial production, the need for metals in the reaction, and low yield, and achieve the possibility of large-scale production , mild reaction conditions and low price

Inactive Publication Date: 2015-12-09
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has good atom economy, the reaction requires metal participation, and the yield is not high, so it is not realistic to realize industrial production

Method used

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  • Preparation method of polysubstituted 2-imino thiazole compound
  • Preparation method of polysubstituted 2-imino thiazole compound
  • Preparation method of polysubstituted 2-imino thiazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of 4-methyl-3-isopropyl-2-isopropyliminothiazole

[0039] (1) Add 0.030g (0.5mmol) isopropylamine, 0.051g (0.5mmol) isopropyl isothiocyanate, 0.120g (0.6mmol) 2,3-dibromopropene to the sealable reaction tube successively, 3mLCH 3 CN, then add 0.265g (1.25mmol) K 3 PO 4 , stirred at room temperature for 0.5h.

[0040] (2) The reaction temperature was raised from room temperature to 60° C., stirred for 3 h, tracked and monitored by TLC, and cooled to room temperature after the reaction was completed.

[0041] (3) Add 4mL15wt% ammonium chloride aqueous solution to the reaction solution to adjust the pH to 8, then extract with ethyl acetate (15mL×3), combine the organic layers, wash with saturated brine, dry over anhydrous sodium sulfate, and spin evaporate After concentration, the concentrate was separated by silica gel column chromatography (eluent: petroleum ether: ethyl acetate = 6:1, volume ratio) to obtain a light yellow liquid product 4-methy...

Embodiment 2

[0045] Example 2: Synthesis of 4-methyl-3-n-butyl-2-butyliminothiazole

[0046] Using 0.036g (0.5mmol) of n-butylamine, 0.058g (0.5mmol) of butyl isothiocyanate and 0.120g (0.6mmol) of 2,3-dibromopropene as raw materials, the preparation method described in Example 1 was followed. Finally, 0.104 g of light yellow liquid product 4-methyl-3-n-butyl-2-butyliminothiazole (1b) was obtained with a yield of 92%.

[0047] 1 HNMR and 13 The CNMR data are as follows.

[0048]

[0049] 1 HNMR (500MHz, CDCl 3 )δ5.52(s,1H),3.74(t,J=7.5Hz,2H),3.08(t,J=7.1Hz,2H),2.08(s,3H),1.67–1.57(m,4H), 1.37(ddd,J=25.9,15.0,7.4Hz,4H),0.93(t,J=7.4Hz,6H). 13 CNMR (125MHz, CDCl 3 )δ158.7, 135.1, 91.2, 54.6, 43.6, 33.0, 30.4, 20.7, 20.1, 14.7, 13.9.

Embodiment 3

[0050] Example 3: Synthesis of 4-methyl-3-n-propyl-2-isopropyliminothiazole

[0051] With 0.030g (0.5mmol) n-propylamine, 0.051g (0.5mmol) isopropyl isothiocyanate and 0.120g (0.6mmol) 2,3-dibromopropene as raw materials, according to the preparation method described in Example 1 . Finally, 0.081 g of light yellow liquid product 4-methyl-3-n-propyl-2-isopropyliminothiazole (1c) was obtained with a yield of 82%.

[0052] 1 HNMR and 13 The CNMR data are as follows.

[0053]

[0054] 1 HNMR (500MHz, CDCl 3 )δ5.44(s,1H),3.70–3.63(m,2H),3.15–3.07(m,1H),2.06(d,J=1.2Hz,3H),1.71–1.62(m,2H),1.17 (d,J=6.2Hz,6H),0.92(t,J=7.5Hz,3H). 13 CNMR (125MHz, CDCl 3 )δ156.8, 135.0, 91.0, 55.8, 45.2, 23.5, 21.4, 14.8, 11.2.

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Abstract

The invention provides a preparation method of a polysubstituted 2-imino thiazole compound shown in the formula IV. In an aprotic polar solvent, primary amine shown in the formula I, isothiocyanate shown in the formula II and substitutional propylene dibromide shown in the formula III are reacted under the action of alkaline substances and on the condition that the reaction temperature ranges from 25 DEG C to 125 DEG C, TLC tracking monitoring is conducted, and after the reaction is completed, the polysubstituted 2-imino thiazole compound shown in the formula IV is obtained after post-treatment is conducted on reaction liquid. The preparation method of the polysubstituted 2-imino thiazole compound is mild in reaction condition, low in cost, high in efficiency, green and environmentally friendly.

Description

(1) Technical field [0001] The invention relates to a preparation method of multi-substituted 2-iminothiazole compounds. (2) Background technology [0002] Thiazole is an important azole compound, which is widely used in many fields such as medicine, pesticide, dye and material. 2-iminothiazole compounds exhibit various biological activities such as antibacterial, antiviral and insecticidal, so they are one of the key development areas of new medicines and pesticides. For example, compound A shown below containing a 2-aminothiazole fragment is an inhibitor of tubulin and can be used to treat cancer, and compound B is a high-performance herbicide. [0003] [0004] In the prior art, the chemical synthesis of many substituted 2-iminothiazole compounds mainly contains the following methods: [0005] Reaction formula (1): Using α-halogenated ketone and thiourea as raw materials, the synthesis of 2-iminothiazole compounds is completed under the promotion of microwave (Tetrah...

Claims

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Application Information

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IPC IPC(8): C07D277/42
CPCC07D277/42
Inventor 金红卫许萌吴庆安高丙杰黄艺伟
Owner ZHEJIANG UNIV OF TECH