Method for synthesizing substituted m-phthalic isothiocyanate by one-pot method, and synthesized substituted m-phthalic isothiocyanate compound

A technology of m-phenylene diisothiocyanate and m-phenylenediamine, which is applied in the field of compound synthesis, can solve the problems of harsh reaction conditions, long reaction time and high production cost, and achieves mild reaction conditions, wide application and reduced cost. Effect

Inactive Publication Date: 2014-09-24
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthetic route is long, the reaction time is long, the production cost is high, the reaction conditions are harsh, the post-processing is difficult, and the yield is low

Method used

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  • Method for synthesizing substituted m-phthalic isothiocyanate by one-pot method, and synthesized substituted m-phthalic isothiocyanate compound
  • Method for synthesizing substituted m-phthalic isothiocyanate by one-pot method, and synthesized substituted m-phthalic isothiocyanate compound
  • Method for synthesizing substituted m-phthalic isothiocyanate by one-pot method, and synthesized substituted m-phthalic isothiocyanate compound

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Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0026] Reaction 1

[0027]

[0028] Compound 1: 2,4-Diisopentyloxym-phenylene diisothiocyanate

[0029] Structural formula:

[0030] Under anhydrous and oxygen-free conditions, the compound 2,4-diisopentyloxy m-phenylenediamine (269mg, 0.96mmol) and Et 3 A solution of N (1.3ml, 9.6mmol) in 11ml of dichloromethane was injected into (0.1ml, 1.3mmol) of thiophosgene in 60ml of dichloromethane, and the injection was completed in 1h. Afterwards, the reaction solution was placed at room temperature for 2 h. The reaction solution was washed successively with saturated sodium bicarbonate and saturated sodium chloride, dried over anhydrous sodium sulfate, and then subjected to petroleum ether / acetone column chromatography to obtain 311 mg of a colorless liquid, which was cooled to a white solid with a yield of 89.1%. 1 H NMR (400MHz, CDCl 3 )δ: 6.72(s,1H),6.37(s,1H),3.99(t,J=6.3Hz,4H),1.92-1.82(m,2H),1.70-1.65(m,4H),0.91(t ,J=6.6Hz,12H). 13 C NMR (100MHz, CDCl 3 )δ: 154.82,...

preparation Embodiment 2

[0042] Reaction 4

[0043]

[0044] Compound 4: n-butylamine 3,5-diisothiocyanate benzoate

[0045] Structural formula:

[0046]

[0047] Under anhydrous and oxygen-free conditions, the compound 3.5-diaminobenzoic acid n-butyramide (198mg, 0.96mmol) and Et 3 A solution of N (1.3ml, 9.6mmol) in 11ml of dichloromethane was injected into (0.1ml, 1.3mmol) of thiophosgene in 60ml of dichloromethane, and the injection was completed in 1h. Afterwards, the reaction solution was placed at room temperature for 2 h. The reaction solution was washed successively with saturated sodium bicarbonate and saturated sodium chloride, dried over anhydrous sodium sulfate, and then subjected to petroleum ether / acetone column chromatography to obtain 261 mg of a white solid with a yield of 93.4%. 1 H NMR (400MHz, CDCl 3 )δ: 7.47(d,J=1.8Hz,2H),7.13(t,J=1.8Hz,4H),6.15(s,1H),3.47-3.42(m,2H),1.64-1.57(m,2H ),1.45-1.36(m,2H),0.96(t,J=7.4Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ: 163.63, 138.26, 136...

preparation Embodiment 3

[0061] Reaction 7

[0062]

[0063] Compound 73, n-octyl 5-diisothiocyanate benzoate

[0064] Structural formula:

[0065]

[0066] Under anhydrous and oxygen-free conditions, at -75°C, the compound 3,5-diaminobenzoic acid n-octyl (253mg, 0.96mmol) and Et3N (1.3ml, 9.6mmol) in 11ml of dichloromethane were injected into (0.1ml, 1.3mmol) of thiophosgene in 60ml of dichloromethane, 1h injection was completed. Afterwards, the reaction solution was placed at room temperature for 2 h. The reaction solution was washed successively with saturated sodium bicarbonate and saturated sodium chloride, dried over anhydrous sodium sulfate, and then subjected to petroleum ether / acetone column chromatography to obtain 321 mg of a colorless liquid, which was cooled to a white solid with a yield of 96.1%. 1 H NMR (400MHz, CDCl 3 )δ7.75(d,J=1.9Hz,2H),7.20(t,J=1.9Hz,1H),4.33(t,J=6.7Hz,2H),1.84–1.70(m,2H),1.41- 1.29(m,10H),0.89(t,J=6.8Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ: 164.04, 139.32,...

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Abstract

The invention relates to the field of compound synthesis, in particular to a method for synthesizing substituted m-phthalic isothiocyanate by a one-pot method, and a synthesized substituted m-phthalic isothiocyanate compound. According to the method, m-phenylenediamine, m-phenylenediamine derivatives and thiophosgene are used as raw materials, triethylamine is used as acid-binding agents, and the one-pot method is used for synthesizing the substituted m-phthalic isothiocyanate. Compared with the prior art, the method provided by the invention utilizes m-phenylenediamine and m-phenylenediamine derivatives and has the advantages that 1) the multi-step reaction is changed into the one-step reaction; 2) the post treatment is simple, and the operation is easy; 3) the reaction condition is mild; 4) the yield is high; 5) the cost is reduced; 6) the micro reaction is changed into the massive reaction, and the method is suitable for industrial production; and 7) the application is wide, and the method is applicable to reaction of various substituted amine.

Description

technical field [0001] The invention relates to the field of compound synthesis. Specifically, the invention relates to a method for synthesizing substituted m-phenylene diisothiocyanate in one pot and the synthesized substituted m-phenylene diisothiocyanate compound. Background technique [0002] Isothiocyanate is an important class of organic synthesis intermediates, widely used in medicine, pesticides, dyes and mineral processing. In medicine, it has antibacterial, anti-inflammatory, anti-cancer and anti-cancer effects; in agriculture, it can be used as antibacterial, insecticide, herbicide, etc.; in mineral processing, it is a new type of high-efficiency and low-toxic copper sulfide ore Collectors. At the same time, isothiocyanate can also participate in a variety of organic reactions, and is used to synthesize various types of compounds containing sulfur, nitrogen, and oxygen, especially heterocyclic compounds, and is widely used in organic synthetic products such as p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C331/30
Inventor 龚兵何兰吴泽辉
Owner BEIJING NORMAL UNIVERSITY
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