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Method for synthesizing isothiocyanate compound through rhodium catalysis
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A technology of ester compounds and isothiocyanate, which is applied in the field of rhodium-catalyzed synthesis of isothiocyanate compounds, can solve the problems of rare synthesis methods, narrow application range, and limited application, and achieve good substrate universality, The synthesis method is simple and the effect of high yield
Active Publication Date: 2022-07-08
SHANGHAI INST OF TECH
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Problems solved by technology
In this method, alkyne halides are used as raw materials. The synthesis of such compounds is extremely difficult, the synthesis methods are rare, the yield is low and the scope of application is narrow, so the application of this method is greatly limited.
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Embodiment 1
[0022]
[0023] Bromobenzene (1.0 mmol), NaSCN (1.2 mmol), and catalyst Rh(acac) were added to the reaction tube in turn 3 (0.03mmol), AgOTf (0.06mmol), then add solvent DMF 2mL, react at 60 ℃ for 6 hours, after the reaction is completed, the reaction solution is concentrated, and the corresponding product is obtained by column chromatography, and the isolated yield is 90%. 1 H NMR (400MHz, CDCl 3 )δ: 7.37 (t, J=7.0 Hz, 2H), 7.30 (d, J=7.5 Hz, 1H), 7.25 (d, J=7.5 Hz, 2H). HRMS theoretical value C 7 H 5 NS(M) + : 135.0143, actual measured value: 135.0149.
Embodiment 2
[0025]
[0026] 4-Methylchlorobenzene (1.0 mmol), NaSCN (1.3 mmol) and catalyst Rh(acac) were added to the reaction tube in sequence 3 (0.02mmol), AgOTf (0.06mmol), then add solvent DMF 2mL, react at 80 ℃ for 10 hours, after the reaction is completed, the reaction solution is concentrated, and the corresponding product is obtained by column chromatography, and the isolated yield is 92%. 1 H NMR (400MHz, CDCl 3 )δ: 7.12(d, J=8.5Hz, 2H), 7.08(d, J=8.5Hz, 2H), 2.37(s, 3H). HRMS theoretical value C 8 H 7 NS(M) + : 149.0299, actual measured value: 149.0302.
Embodiment 3
[0028]
[0029] 2-methylchlorobenzene (1.0 mmol), KSCN (1.5 mmol) and catalyst Rh(acac) were added to the reaction tube in sequence 3 (0.05mmol), AgOTf (0.10mmol), then added solvent DMF 2mL, reacted at 70 ℃ for 5 hours, after the reaction was completed, the reaction solution was concentrated, and the corresponding product was obtained by column chromatography, and the isolated yield was 88%. 1 H NMR (400MHz, CDCl 3 )δ: 7.27 (d, J=8.0 Hz, 1H), 7.15 (d, J=8.0 Hz, 1H), 7.09-7.03 (m, 2H), 2.39 (s, 3H). HRMS theoretical value C 8 H 7 NS(M) + : 149.0299, actual measured value: 149.0303.
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Abstract
The invention relates to a method for catalytically synthesizing an isothiocyanate compound by rhodium, which comprises the following steps: by taking rhodium acetylacetonate Rh (acac) 3 as a catalyst, dissolving halogenated hydrocarbon and thiocyanate in DMF (Dimethyl Formamide) in the presence of silver salt, reacting, separating and purifying to obtain the target product isothiocyanate compound. Compared with the prior art, the synthesis method disclosed by the invention is simple and green, and the isothiocyanate compound and the like are directly synthesized by using cheap and easily available raw materials, namely halogenated hydrocarbon and stable inorganic salt thiocyanide.
Description
technical field [0001] The invention belongs to the technical field of chemical synthesis, and relates to a method for synthesizing isothiocyanate compounds catalyzed by rhodium. Background technique [0002] Isothiocyanates and their derivatives are important raw materials for the synthesis of nitrogen- or sulfur-containing heterocyclic compounds. Many natural and synthetic isothiocyanates have strong biological activities, such as antibacterial and anti-inflammatory, antioxidant, anti- It has been widely used in the preparation of pharmaceuticals, pesticides, dyes and other industrial products. The traditional synthesis method of this type of compound is to use primary amine as raw material, react it with thiophosgene or carbon disulfide or phenyl thiochloroformate to react isothiocyanate, but these reactions usually use more toxic reagents as Raw materials have higher requirements on production equipment, and the production process also has higher risks, and these reacti...
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