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A kind of preparation method of thiocarbamate compound

A thiocarbamate and compound technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry and other directions, can solve problems such as unfavorable actual production, complicated and tedious operations, unstable and easy to oxidize, etc., to avoid metal reagents. Efficacy of use, process safety, avoidance of toxic phosgene and carbon monoxide use

Active Publication Date: 2020-08-11
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above two types of methods also have obvious shortcomings: method (1) needs to use metal catalysts and oxidants to mediate the reaction of thiophenol and sulfinate in advance to prepare thiosulfonate raw materials, the operation is complicated and cumbersome, the cost is large, and the reaction produces The equivalent waste sulfinate ester is difficult to deal with after the reaction; method (2) directly uses unstable, easily oxidized and smelly thiophenols or mercaptans, without using actual production

Method used

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  • A kind of preparation method of thiocarbamate compound
  • A kind of preparation method of thiocarbamate compound
  • A kind of preparation method of thiocarbamate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] At room temperature, add sodium benzene sulfinate (0.2 mmol), ethyl isonitrile (0.4 mmol), water (0.6 mmol), acetonitrile (1.5 mL), molecular iodine (0.02 mmol), And dimethyl phosphite (0.4mmol), mix well, and then at 100 o After heating and stirring the reaction for 6 hours under C condition, the reaction was detected by TLC until the completion of the reaction, 2 mL of water was added, and then extracted with ethyl acetate (4 mL) for 3 times. The extract was concentrated under reduced pressure under 0.08 Mpa to solvent-free to obtain the crude product. Then it was washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5:1, and flash column chromatography on a silica gel column to obtain 83% thiocarbamate and 39.7 mg of white solid.

[0030] 1 H NMR (500 MHz, CDCl 3 ): δ 7.61 – 7.59 (m, 2H), 7.47 – 7.42 (m, 3H),6.00 (s, 1H), 4.21 (q, J = 7.2 Hz, 2H), 4.04 (d, J = 5.1 Hz, 2H), 1.28 (t, J = 7.2 Hz, 3H); 13 C NMR (125 MHz, CDCl 3 ): ...

Embodiment 2

[0032]

[0033] At room temperature, add sodium benzene sulfinate (0.2 mmol), ethyl isonitrile (0.4 mmol), water (0.6 mmol), ethyl acetate (1.5 mL), and molecular iodine (0.02 mmol) into a 25 mL reaction tube. ), and diethyl phosphite (0.4mmol), mix well, and then at 100 o After the reaction was heated and stirred for 6 hours under C condition, the reaction was detected by TLC, 2 mL of water was added, and then extracted with ethyl acetate (4 mL) three times. The extract was concentrated under vacuum at 0.08Mpa to solvent-free to obtain the crude product. Then it was washed with a mixed eluent of petroleum ether and ethyl acetate at a volume ratio of 5:1, and flash column chromatography on a silica gel column to obtain 75% thiocarbamate and 35.9 mg of white solid.

Embodiment 3

[0035]

[0036] At room temperature, add sodium benzene sulfinate (0.2 mmol), ethyl isonitrile (0.4 mmol), water (0.6 mmol), ethyl acetate (1.5 mL), and molecular iodine (0.02 mmol) into a 25 mL reaction tube. ), and diisopropyl phosphite (0.4mmol), mix well, and then at 100 o After the reaction was heated and stirred for 6 hours under C condition, the reaction was detected by TLC, 2 mL of water was added, and then extracted with ethyl acetate (4 mL) three times. The extract was concentrated under vacuum at 0.08Mpa to solvent-free to obtain the crude product. Then it was washed with a mixed eluent of petroleum ether and ethyl acetate in a volume ratio of 5:1, and flash column chromatography on a silica gel column to obtain 60% thiocarbamate and 28.7 mg of white solid.

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Abstract

The invention belongs to the field of synthesis of a compound, relates to a preparation method of a thiocarbamate compound, in particular to a method for synthesizing thiocarbamate through reacting ofcatalyzing three components of sodium sulfinate, isonitrile and water by iodine. The method comprises the following steps: adding the sodium sulfinate, the isonitrile and the water into ethyl acetate, then adding a molecular iodine catalyst and a phosphite reducing agent, heating, stirring and reacting for 6 to 10 hours under a condition that the temperature is 80 to 100 DEG C, and extracting, separating and purifying after finishing the reaction, thus obtaining the thiocarbamate. According to the method disclosed by the invention, the isonitrile is adopted as a carbon source, so that poisonous photogene and carbon monoxide are prevented from being used; odorless sodium sulfinate is adopted as a sulfur source, so that odorous thiophenol or thiol is prevented from being used; non-metalliciodine is adopted for catalyzing, so that a metal reagent is prevented from being used; the reaction has the advantages that the operation is simple and convenient, the technology is safe, environmentfriendliness is realized, and the like.

Description

Technical field [0001] The invention belongs to the field of compound synthesis, and relates to a preparation method of a thiocarbamate compound, in particular to a method for synthesizing thiocarbamate by iodine-catalyzed three-component reaction of sodium sulfinate, isonitrile and water. Background technique [0002] Thiocarbamates are an important class of organic compounds, which have a wide range of applications in medicinal chemistry, biochemistry and pesticide science. In medicinal chemistry, it can be used as anesthetics, fungicides and antiviral agents; in biology, it can be used as biological regulators and enzyme inhibitors; in pesticides, it can be used as insecticides and herbicides. In addition, in synthetic chemistry, thiocarbamate is also an important type of synthon, participating in a variety of reactions, so its synthesis method has always attracted attention. [0003] Traditional synthetic methods of thiocarbamate compounds mainly include hydrolysis and alcohol...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C331/06C07C333/04C07D333/34C07B45/00
CPCC07B45/00C07C331/06C07C333/04C07C2601/14C07D333/34
Inventor 魏伟鲍鹏丽吕玉芬王桦
Owner QUFU NORMAL UNIV
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