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Benzoxazole-2-acrylate and synthesis method thereof

A technology of benzoxazole and acrylate, applied in the direction of organic chemistry, can solve the problems of expensive catalyst, high reaction temperature, low yield, etc., and achieve the effect of good atom economy, strong fluorescence, and easy operation

Active Publication Date: 2020-06-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] More than two kinds of methods for synthesizing benzoxazole-2-acrylate, the catalyst is expensive, the reaction temperature is high, and the productive rate is lower

Method used

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  • Benzoxazole-2-acrylate and synthesis method thereof
  • Benzoxazole-2-acrylate and synthesis method thereof
  • Benzoxazole-2-acrylate and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 5mL of 1,4-dioxane to a 25mL pressure-sealed tube as a solvent, then add 3-(2-isocyanophenoxy)methyl acrylate (1a, 0.5mmol), n-butyl Phosphorus (0.15 mmol) two reactants, the pressure tube was sealed, reacted at 120° C., followed and detected by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA=10:1) to obtain the target product 2a (83 mg, 82% yield).

[0025] The structural formula of compound 2a is:

[0026]

[0027] Molecular formula: C 11 h 9 NO 3

[0028] Chinese name: benzoxazole-2-methyl acrylate; (E)-3-(2-benzoxazole)-methyl acrylate

[0029] English name: (E)-methyl 3-(benzo[d]oxazol-2-yl)acrylate

[0030] Molecular weight: 203.1941

[0031] Appearance: white solid

[0032] Melting point: 105-106°C

[0033] Proton NMR spectrum: 1 HNMR (500MHz, CDCl 3 ): δ (ppm) = 7.76 (d, J = 7.0Hz, 1H), 7.57 (d, J = 16.0Hz, 1H), 7.54 (d...

Embodiment 2

[0037] Add 5mL of 1,4-dioxane to a 25mL pressure-sealed tube as a solvent, and then add 3-(2-isocyano-6-methylphenoxy)methyl acrylate (1b, 0.5mmol ), n-butylphosphine (0.15mmol) two reactants, the pressure tube was sealed, reacted at 120°C, and tracked and detected by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA=10:1) to obtain the target product 2b (61 mg, 56% yield).

[0038] The structural formula of compound 2b is:

[0039]

[0040] Molecular formula: C 12 h 11 NO 3

[0041] Chinese name: 7-methylbenzoxazole-2-methyl acrylate-; (E)-3-[2-(7-methylbenzoxazole)]-methyl acrylate

[0042] English name: (E)-methyl 3-(7-methylbenzo[d]oxazol-2-yl)acrylate

[0043] Molecular weight: 217.2206

[0044] Appearance: white solid

[0045] Melting point: 91-92°C

[0046] Proton NMR spectrum: 1 H NMR (500MHz, CDCl 3 ): δ(ppm)=7.60-7.56(m,3H),7.26(t...

Embodiment 3

[0050] Add 5 mL of 1,4-dioxane to a 25 mL pressure-sealed tube as a solvent, and then add 3-(2-isocyano-5-fluoro-phenoxy)methyl acrylate (1c, 0.5 mmol ) and n-butylphosphine (0.15 mmol), the pressure-resistant tube was sealed and reacted at 120° C., followed by detection by TLC until the end of the reaction. The reaction system was rotary evaporated under vacuum to obtain a concentrate, which was separated by column chromatography (eluent: PE:EA=10:1) to obtain the target product 2c (78 mg, 71% yield).

[0051] The structural formula of compound 2c is:

[0052]

[0053] Molecular formula: C 12 h 11 NO 3

[0054] Chinese name: -6-fluorobenzoxazole-2-methyl acrylate; (E)-3-[2-(6-fluorobenzoxazole)]-methyl acrylate

[0055] English name: (E)-methyl 3-(6-fluorobenzo[d]oxazol-2-yl)acrylate

[0056] Molecular weight: 221.1845

[0057] Appearance: white solid

[0058] Melting point: 121-122°C

[0059] Proton NMR spectrum: 1 H NMR (500MHz, CDCl 3 ): δ (ppm) = 7.70 (dd, J...

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Abstract

The invention discloses a benzoxazole-2-acrylate compound and a synthetic method thereof. The compound is characterized in that the structure of the compound is shown in the invention, wherein R1 is H, methyl, ester group or halogen element; and R2 is methyl or ethyl. According to the invention, through a cyclization reaction of 3-(2-isocyanophenoxy) acrylate under the catalysis of n-butyl, the aromatic ring substituted 2-acrylate benzoxazole compound can be synthesized through the cyclization reaction. The reaction can be smoothly carried out without a transition metal catalyst, the reactioncondition is mild, the experimental operation is simple and convenient, and the atom economy is good. The method provides a new synthetic route for synthesis of aromatic ring substituted benzoxazole-2-acrylate, and has potential application value in organic synthesis.

Description

technical field [0001] The invention relates to a benzoxazole-2-acrylate and a synthesis method thereof. Background technique [0002] Most of the 2-substituted benzoxazole compounds have unique physiological activity and strong fluorescence, and have a wide range of applications in the fields of sterilization, anti-corrosion, anti-tumor, dyes, fluorescent whitening, etc., so there are many studies on their synthesis methods. However, there are few reports on the synthesis of benzoxazole-2-acrylate. There are two following methods for the synthesis of benzoxazole-2-acrylate reported in the literature in recent years: [0003] Lee et al obtained benzoxazole-2-acrylate through the cross dehydrogenation coupling of benzoxazole and acrylate. In the reaction of benzoxazole and acrylate in Pd(TFA) 2 As a catalyst, phenanthrene as a ligand, under the action of 2.0 equivalents of oxidant AgTFA, 2-acrylate benzoxazole was obtained by reacting in toluene at 130 ° C, but two example...

Claims

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Application Information

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IPC IPC(8): C07D263/56
CPCC07D263/56
Inventor 苏世宽李健王志爽费友文陈雅丽
Owner SHANGHAI UNIV