Preparation method of phenyl dithiourea compound

A technology of phenyldithiourea and compounds, which is applied in the field of COF monomer synthesis, can solve the problems of low yield, poor practicability, and poor universality, and achieve the effects of high yield, expanded structural diversity, and low cost

Pending Publication Date: 2022-06-21
ZHONGYUAN ENGINEERING COLLEGE
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Problems solved by technology

[0005] Through the above analysis, the problems and defects of the prior art are: the existing preparation method has poor universality, low yield, harsh reaction conditions and is not suitable for scale-up production, and poor practicability

Method used

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  • Preparation method of phenyl dithiourea compound
  • Preparation method of phenyl dithiourea compound
  • Preparation method of phenyl dithiourea compound

Examples

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preparation example Construction

[0039] like figure 1As shown, the present invention provides a preparation method of a phenylbisthiourea compound, comprising the following steps:

[0040] S101, in an organic solvent, the phenylenediamine compound, the organic phosphine compound and the iodide are mixed uniformly, and under nitrogen protection, trifluoromethanesulfonyl chloride is slowly added at 0°C, and the reaction is carried out at room temperature for 1-4 hours.

[0041] S102, drop to 0°C, slowly add ammonia water, stir for 5-30min, raise the temperature to 50°C, and continue the reaction for 0.5-2h.

[0042] S103, centrifuging, washing and purifying with an organic solvent used for processing, and vacuum drying to obtain the obtained product.

[0043] In a preferred embodiment, the iodide is one of sodium iodide, potassium iodide, amine iodide, lithium iodide, cesium iodide and iodine, and the organic phosphine compound is: triphenylphosphine, One of tricyclohexylphosphine, tris(o-methylphenyl)phosphi...

Embodiment 1

[0055] The preparation method embodiment 1 of the 1,4-benzenedithiourea compound of the present invention, the synthetic route is as follows:

[0056]

[0057] Synthesis steps: in 50mL DMF, mix 10mmol of 1,4-phenylenediamine, 25mmol of tricyclohexylphosphine, and 24mmol of potassium iodide. The reaction was carried out for 3h. Drop to 0°C, slowly add ammonia water, stir for 10min, raise the temperature to 50°C, and continue the reaction for 1h. It was centrifuged, purified by washing with THF and water, and dried in vacuo to obtain 1.94 g of a white solid product with a yield of 86%.

[0058] The H NMR and C spectra of the product are as figure 2 and image 3 As shown, the characterization data is: 1 H NMR (400MHz, deuterated DMSO) δ 9.61 (s, 2H), 7.30 (s, 8H); 13 C NMR (100 MHz, deuterated DMSO) δ 181.5, 136.0, 124.2.

Embodiment 2

[0060] The difference between this example and Example 1 is that the solvent used in the reaction is acetonitrile, the organic phosphine is triphenylphosphine, and the yield is 56%.

[0061] Other steps in this embodiment are the same as those in Embodiment 1, and are not repeated here.

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Abstract

The invention belongs to the technical field of COF monomer synthesis, and discloses a preparation method of a phenyl dithiourea compound. The preparation method comprises the following steps: uniformly mixing a phenylenediamine compound, an organic phosphine compound and iodide in an organic solvent, slowly adding trifluoromethanesulfonyl chloride at 0 DEG C under the protection of nitrogen, and reacting at room temperature for 1-4 hours; cooling to 0 DEG C, slowly adding ammonia water, stirring for 5-30 minutes, heating to 50 DEG C, and continuously reacting for 0.5-2 hours; and carrying out centrifugal separation, washing and purifying with an organic solvent for treatment, and carrying out vacuum drying to obtain the phenyl dithiourea compound. According to the preparation method of the phenyl dithiourea compound, one-pot reaction preparation is adopted, the process is mild and easy to control, the purity and yield of the product are high, the substrate universality is high, aftertreatment is simple and rapid, and the product can be prepared on an amplification scale. Due to the advantages, the preparation cost of the phenyl dithiourea compound is remarkably reduced, and the phenyl dithiourea compound has good industrial application value.

Description

technical field [0001] The invention belongs to the technical field of COF monomer synthesis, and discloses a preparation method of a phenylbisthiourea compound. Background technique [0002] A variety of covalent bonding methods such as C-N, N-N, B-N, C-C and B-O are used to construct the framework of COF. However, there are only two reported COFs connected by thiourea structure in the past year (H.L.Qian, M.S.Zhu, M.L.Du.X.Q.Ran, X.P.Yan, J.Hazard.Mater., 2022, 427, 128156 ; B.W.Ma, C.Z.Li, L.Zhang, L.P.Zhai, F.J.Hu, Y.M.Xu, H.J.Qiao, Z.Wang, W.Y.Ai, L.W.Mi, CrystEngComm, 2021, 23, 7576.), the reason is that the material constituting thiourea COFs The difficulty of thiourea monomer synthesis. [0003] We know that phenylbisthiourea compounds can be used as reactive monomers to synthesize COFs. For example, 1,4-phenylbisthiourea (CAS: 1519-70-6) is relatively cheap on the market, and phenylbisthiourea compounds substituted by other substituents are rarely provided by sup...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C335/16C08G12/12
CPCC07C335/16C08G12/12
Inventor 马佰位艾文英翟黎鹏胡富佳许艺蒙米立伟
Owner ZHONGYUAN ENGINEERING COLLEGE
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