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Isothiocyanate synthesized by three components and preparation method of isothiocyanate

An isothiocyanate and three-component technology, applied in the field of three-component synthetic isothiocyanate and its preparation, can solve the problems of limited practicability and applicability, long reaction time, cumbersome processing, etc. Ensuring the health of operators, strong substrate universality, and simplifying the effect of process engineering

Inactive Publication Date: 2019-04-12
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these reactions have harsh conditions, need to be carried out step by step, the reaction time is long, and the processing is cumbersome; due to the existence of these defects, the practicability and applicability of these methods have been greatly limited.

Method used

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  • Isothiocyanate synthesized by three components and preparation method of isothiocyanate

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0033] Specific embodiment one: with 28.6 milligrams (0.2mmol) 2-naphthylamine (1.0 equivalent), 1.9 milligrams (0.01mmol) cuprous iodide (5% equivalent), 59.2 milligrams (0.3mmol) sodium difluorobromoacetate (1.5 equivalent), 51.2 mg (0.2 mmol) S 8 (1.0 equiv), 84.9 mg (0.004 mmol) of potassium phosphate (2% equiv), was added to 2 mL of solvent acetonitrile. React at 100°C for 12 hours, cool down after the reaction, filter the reaction liquid to obtain the filtrate, then perform rotary evaporation on the filtrate, remove the solvent to obtain the residue, and use silica gel column chromatography to elute the residue with petroleum ether as the eluent , collected the effluent, detected by TLC, combined the effluent containing the product, distilled off the solvent with a rotary evaporator, and dried in vacuo to obtain 32.2 mg of 2-naphthalene isothiocyanate as a white solid with a yield of 87%. m.p.116-118℃. 1 H NMR (400MHz, CDCl 3 )δ7.83-7.80 (m, 2H), 7.77 (d, J = 8.0Hz, 1...

specific Embodiment 2

[0034] Specific embodiment two: with 28.6 milligrams (0.2mmol) 1-naphthylamine (1.0 equivalent), 1.9 milligrams (0.01mmol) cuprous iodide (5% equivalent), 59.2 milligrams (0.3mmol) sodium difluorobromoacetate (1.5 equivalent), 51.2 mg (0.2 mmol) S 8 (1.0 equiv), 84.9 mg (0.004 mmol) of potassium phosphate (2% equiv), was added to 2 mL of solvent acetonitrile. React at 100°C for 12 hours, cool down after the reaction, filter the reaction liquid to obtain the filtrate, then perform rotary evaporation on the filtrate, remove the solvent to obtain the residue, and use silica gel column chromatography to elute the residue with petroleum ether as the eluent , collected the effluent, detected by TLC, combined the effluent containing the product, distilled off the solvent with a rotary evaporator, and dried in vacuo to obtain 30.0 mg of 1-naphthalene isothiocyanate as a white solid with a yield of 81%. m.p.53-55℃; 1 H NMR (400MHz, CDCl 3 )δ8.10(d, J=8.0Hz, 1H), 7.87(d, J=8.0Hz, 1H)...

specific Embodiment 3

[0035] Specific example three: with 18.6 milligrams (0.2mmol) aniline (1.0 equivalent), 1.9 milligrams (0.01mmol) cuprous iodide (5% equivalent), 59.2 milligrams (0.3mmol) sodium difluorobromoacetate (1.5 equivalent), 51.2 mg (0.2 mmol) S 8 (1.0 equiv), 84.9 mg (0.004 mmol) of potassium phosphate (2% equiv), was added to 2 mL of solvent acetonitrile. React at 100°C for 12 hours, cool down after the reaction, filter the reaction liquid to obtain the filtrate, then perform rotary evaporation on the filtrate, remove the solvent to obtain the residue, and use silica gel column chromatography to elute the residue with petroleum ether as the eluent , collected the effluent, detected by TLC, combined the effluent containing the product, distilled off the solvent with a rotary evaporator, and dried in vacuo to obtain 22.4 mg of phenyl isothiocyanate, with a yield of 83%. 1 HNMR (400MHz, CDCl 3 )δ7.40(t, J=7.4Hz, 2H), 7.33(t, J=7.4HZ, 1H), 7.29-7.26(m, 2H); 13 CNMR (125MHz, CDCl 3 ...

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Abstract

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, and more specifically relates to a three-component synthesized isothiocyanate and a preparation method thereof. Background technique [0002] As a class of important organic molecules with high biological performance and chemical activity, isothiocyanates are widely used in fields such as medicine, biochemistry, and organic synthesis (see Curr.Med.Chem., 2008, 15, 440 and Phytochem .Rev., 2009,8,269. For example, many isothiocyanates have anticancer, anti-inflammatory, antibacterial and antiplatelet effects (seeing Proc.Natl.Acad.Sci.U.S.A., 1992,89,2399 and Drug Metab.Rev., 2015, 47, 356). In addition, isothiocyanates are also commonly used as precursors for the synthesis of food additives and drug molecules (see Org.Lett.2017, 19, 2166). [0003] The preparation method of isothiocyanate mainly contains following several approaches: thiophosgene synthetic method: generate isothiocyanat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/00C07C331/20C07C331/24C07C331/26C07C331/28C07D209/08
CPCC07B45/00C07C331/20C07C331/24C07C331/26C07C331/28C07D209/08C07C2601/14
Inventor 张兴国韦锋王随乾张小红
Owner WENZHOU UNIVERSITY
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