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Preparation method of thiophosphate compounds

A technology of phosphorothioate and thiol compounds, which is applied in the field of preparation of phosphorothioate compounds, can solve the problems of unfavorable large-scale production, long reaction time, and metal residue, and achieve less by-products and short reaction time , the effect of mild reaction conditions

Inactive Publication Date: 2017-07-07
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] However, with this process route, heating or metal catalysts are still required for the synthesis of phosphorothioate, and the reaction time is longer, which will not only bring metal residues, but also is not conducive to large-scale industrial production.

Method used

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  • Preparation method of thiophosphate compounds

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preparation example Construction

[0054] The invention provides a kind of preparation method of phosphorothioate compound, comprises the following steps:

[0055] A) Under the action of an inorganic base, react P(O)-H compounds and compounds containing mercapto functional groups in an organic solvent to obtain phosphorothioate compounds.

[0056] The present invention has no special restrictions on the P(O)-H compounds, and the definition of P(O)-H compounds well-known to those skilled in the art can be used. Those skilled in the art can according to actual production conditions, raw material conditions and Product requirements are selected and adjusted. The P(O)-H compounds described in the present invention can be called phosphite compounds. In this field, the structure of such compounds can also include those that do not contain ester group structures Compound, more preferably refers to a class of compounds containing P (O)-H chemical bonds, specifically can be one of dialkyl phosphite, diaryl phosphite, di...

Embodiment 1

[0099] Synthesis of diethyl p-methylphenylphosphorothioate

[0100]

[0101] Weigh 0.5mmol of diethyl phosphite, 0.25mmol of potassium carbonate, and 0.75mmol of p-methylthiophenol into a 10mL round-bottomed flask, add magnetons and 3mL of tetrahydrofuran, and stir for 6 hours at room temperature. The tetrahydrofuran solvent was removed, and the residue was dissolved with 1 mL of dichloromethane. The residue was purified by silica gel column analysis to obtain a colorless transparent liquid with a yield of 62%.

[0102] see figure 1 , figure 1 It is the H NMR spectrum of p-methylphenyl diethyl phosphorothioate prepared in Example 1 of the present invention.

[0103] Depend on figure 1 It can be seen that:

[0104] 1 H NMR (400MHz, CDCl 3 )δ7.45–7.42(m,2H),7.16–7.12(m,2H),4.33–4.03(m,4H),2.34(d,J=1.5Hz,3H),1.30(t,J=7.1Hz ,6H); 13 C NMR (100MHz, CDCl 3 )δ139.2(d, J=3.1Hz), 134.5(d, J=5.0Hz), 130.1(d, J=2.4Hz), 122.8(d, J=7.3Hz), 63.9(d, J=6.2 Hz), 21.1(d, J=0.8Hz), ...

Embodiment 2

[0106] Synthesis of dimethyl p-methylphenylphosphorothioate

[0107]

[0108] Weigh 0.5mmol of dimethyl phosphite, 0.25mmol of potassium carbonate, and 0.75mmol of p-methylthiophenol into a 10mL round-bottomed flask, add magnetons and 3mL of tetrahydrofuran, and stir for 6 hours at room temperature. The tetrahydrofuran solvent was removed, and the residue was dissolved with 1 mL of dichloromethane. The residue was purified by silica gel column analysis to obtain a colorless transparent liquid with a yield of 55%.

[0109] see figure 2 , figure 2 It is the H NMR spectrum of the p-methylphenyl dimethyl phosphorothioate prepared in Example 2 of the present invention.

[0110] Depend on figure 2 It can be seen that:

[0111] 1 H NMR (CDCl 3 ,400MHz): δ7.45–7.42(m,2H),7.17–7.14(m,2H),3.81(d,J=12.6Hz,6H),2.34(d,J=1.5Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ139.5(d, J=3.2Hz), 134.6(d, J=5.0Hz), 130.2(d, J=2.4Hz), 122.2(d, J=7.4Hz), 54.1(d, J=6.0 Hz), 21.2(d, J=0.7Hz); 31 P ...

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Abstract

The invention provides a method for preparing phosphorothioate compounds, which comprises the following steps: under the action of an inorganic base, reacting a P(O)-H compound and a compound containing a mercapto functional group in an organic solvent to obtain Phosphorothioate compounds. Under the action of inorganic bases, the present invention adopts P(O)-H compounds as initial raw materials, and realizes high-yield phosphorothioate or organophosphate through dehydrogenation coupling reaction under metal-free catalysis and room temperature conditions. Synthetic, and all have good applicability to the alkyl phosphite of different substituting groups or aryl phosphine oxide and thiophenol; The synthetic route that the present invention provides, raw material is simple, and reaction condition is gentle, and reaction time is short, and productive rate High, less by-products, which is conducive to the later synthesis of some biologically active phosphorothioate drugs, reduces metal residues and toxic effects, and provides more directions and options for related applications in drugs, pesticides, and bioactive molecules .

Description

technical field [0001] The invention relates to the technical field of organophosphorus synthesis, and relates to a preparation method of phosphorothioate compounds. Background technique [0002] Phosphorus has a typical non-metallic property. In the process of chemical bonding, phosphorus atoms can not only use 3p orbitals, but also empty 3d orbitals with lower energy can participate in bonding. Therefore, in phosphorus compounds, the valence states of phosphorus atoms are abundant. , its coordination number can be 1, 2, 3, 4, 5, 6, up to 10. my country has abundant reserves of phosphorus resources, but its own utilization rate is low, most of which are mainly exported to ore, and the added value is not high, resulting in a serious waste of resources. Therefore, the active development of organic phosphorus chemical industry and the development of methods for synthesizing high value-added phosphorus chemicals have positive significance for changing the current situation of ...

Claims

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Application Information

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IPC IPC(8): C07F9/40C07F9/32
CPCC07F9/4021C07F9/3229C07F9/3282C07F9/4075C07F9/4084
Inventor 晏鑫星陈迁温春晓曾洁坤黄昱霖王肖峰陈梓铭霍延平杜志云张焜
Owner GUANGDONG UNIV OF TECH
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