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Method for preparing alpha-phosphoramidate compound

A compound and phosphite technology, applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of difficult recycling and catalyst preparation The process is complicated and cannot be recycled, etc.

Active Publication Date: 2019-04-12
盐城锦明药业有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have the following one or more disadvantages: (1) the preparation process of the catalyst is complicated and difficult to recycle; (2) the catalyst has poor stability to air or water and cannot be recycled; (3) the reaction time is long , yield is not high; (4) can only be suitable for laboratory or small-scale operation, does not possess large-scale industrial application; (5) reaction needs organic solvent as reaction medium etc.

Method used

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  • Method for preparing alpha-phosphoramidate compound
  • Method for preparing alpha-phosphoramidate compound
  • Method for preparing alpha-phosphoramidate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Preparation of catalyst (ionic liquid):

[0082] Put 7.91g of triethylamine and 15.10g of trinitromethane in a 100mL round-bottomed flask and stir for 1-2 hours at normal temperature and pressure to obtain 23.01g of yellow liquid with a yield of 100%.

Embodiment 2

[0084] In a 25mL round bottom flask, add 10mmol (1.06g) benzaldehyde, 10.2mmol (0.95g) aniline, 10.3mmol (1.28g) trimethyl phosphite, 0.5mmol the catalyst prepared by Example 1, room temperature (15 ~25°C) for stirring and reacting for 30 minutes, adding water to quench the reaction, filtering, washing, and recrystallizing with an appropriate amount of ethanol to obtain α-anilino-benzyl dimethyl phosphate with a yield of 95%. The aqueous phase was washed twice with 2 mL of ethyl acetate, separated, and distilled at atmospheric pressure to recover the catalyst.

Embodiment 3

[0086] In a 250mL round bottom flask, add 10mmol (1.36g) 4-methoxybenzaldehyde, 10mmol (1.38g) 4-nitroaniline, 12mmol (1.32g) trimethyl phosphite, 0.01mmol catalyst, room temperature ( Stir the reaction at 15~25°C for 30 minutes, add water to quench the reaction, filter, wash, and recrystallize with an appropriate amount of ethanol to obtain α-(4-nitroanilino)-(4-methoxyphenyl)methylphosphoric acid di Methyl ester, yield 95%. The aqueous filtrate was washed twice with 2 mL of ethyl acetate, separated, and the water was distilled off under reduced pressure at a vacuum of 0.095 MPa to recover the catalyst.

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Abstract

The invention provides a method for preparing an alpha-phosphoramidate compound. The method comprises the step of subjecting aromatic aldehyde, amine and phosphite to a tri-ingredient domino reactionunder the condition of ionic liquid, thereby preparing the alpha-phosphoramidate compound. The process conditions are simple, the operability is high, and thus, a novel scheme is provided for large-scale production of the alpha-phosphoramidate compound.

Description

technical field [0001] The present invention relates to a method for preparing α-phosphoramidate compounds, specifically, under the condition of ionic liquid catalyst, aromatic aldehyde, amine and phosphite undergo three-component domino reaction to prepare α-phosphoramidate . Background technique [0002] α-phosphoramidate compounds have good anti-plant virus, inhibitory enzyme activity, anti-tumor, herbicide, bactericidal and other important biological activities, and have a wide range of uses in biochemistry and medicinal chemistry. For example, it can be used as a polymerization inhibitor enzyme, an antibiotic and a pharmacological medium, a herbicide, a hapten-catalyzed antibody, etc., and it is also an important substrate for the synthesis of phosphono-peptides. In addition, α-phosphoramidate compounds are also phosphorus-nitrogen synergistic combustion accelerants, which have wide application value and prospects in polyurethane foam materials. Therefore, its synthet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40B01J31/02C08K5/5353C08L75/04
CPCB01J31/0279B01J31/0298C07F9/4056C07F9/4075C08K5/5353C08L75/04
Inventor 雷泽霄冯雪馨杨锦明方东王庆东赵玉军杨子健
Owner 盐城锦明药业有限公司
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