Preparation method of S-glycidylphthalimide

A technology of glycerin phthalimide and phthalimide, applied in the direction of organic chemistry, etc., can solve the problems of unsuitable industrial production and increased risk factor

Active Publication Date: 2013-11-06
CHENGDU GUOHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the microwave reaction is a closed system reaction, it has certain risks and is only suitable for a small amount of laboratory synthesis. After the scale-up production, the risk factor will increase greatly, and it is not suitable for industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 85g (0.46 mol) of potassium phthalimide, 10.5g (0.046 mol) of benzyltriethylammonium chloride, 0.76g (0.0046 mol) of potassium iodide, and 382.5ml of isopropanol to a 1L single-neck bottle, and stir Evenly, add 85.6g (0.93 mol) of (S) epichlorohydrin to the reaction system at 28°C with stirring, the system changes from white turbid to pale yellow turbid, react at 28°C for 72 hours, After suction filtration, washing with water, and drying, 88.1 g of solid was finally obtained, with a yield of 94.5% and a purity of 92%.

Embodiment 2

[0038] Add 85g (0.46 mol) of potassium phthalimide, 10.5g (0.046 mol) of benzyltriethylammonium chloride, 0.76g (0.0046 mol) of potassium iodide, and 382.5ml of isopropanol to a 1L single-neck bottle, and stir Evenly, add 85.6g (0.93 mol) of (S) epichlorohydrin to the reaction system at 32°C with stirring. The system changes from white turbid to pale yellow turbidity. React at 32°C for 72 hours. After suction filtration, washing with water, and drying, 87.7 g of solid was finally obtained, with a yield of 94.0% and a purity of 90%.

Embodiment 3

[0040] Add 85g (0.46 mol) of potassium phthalimide, 10.5g (0.046 mol) of benzyltriethylammonium chloride, 0.76g (0.0046 mol) of potassium iodide, 850ml of isopropanol to a 1L single-necked flask, and stir well. Add 85.6g (0.93 mol) of (S) epichlorohydrin to the reaction system at 30°C and stirring, the system changes from white turbid to pale yellow turbidity, react for 110 hours at 30°C, pump After filtering, washing with water, and drying, 85.4 g of solid was finally obtained with a yield of 91.5% and a purity of 89%.

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PUM

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Abstract

The invention relates to a preparation method of S-glycidylphthalimide. The preparation method is characterized in that in a reaction of potassium phthalimide or phthalimide and (S) epichlorohydrin, a phase transfer catalyst and potassium iodide are used so that S-glycidylphthalimide synthesis is realized. Compared with the prior art, the preparation method greatly improves an S-glycidylphthalimide yield, has simple and safe processes, produces high-purity products, has a low cost and is suitable for industrial production of S-glycidylphthalimide.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a preparation method of S-glycidyl phthalimide. Background technique [0002] S-glycidyl phthalimide is an important intermediate for the preparation of oxazolidinone compounds such as the new antibiotic linezolid and the new oral anticoagulant drug rivaroxaban, as well as the preparation of antifungal thiooxazolidine Ketones, oxazolidinedione, amide compounds used as growth hormone secretagogues, important intermediates of heterocyclic compounds such as morpholino urea derivatives used to treat inflammation. [0003] The preparation method of S-glycidyl phthalimide is usually synthesized by the method described in Tetrahedron Asym.1996,7,1641 by A.Gutcait et al. The method is based on phthalimide and (S) epichlorohydrin as raw materials, in diethyl azodicarboxylate (DEAD) and triphenylphosphine (PH 3 In the presence of P), tetrahydrofuran was used as a solvent and reacted for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D263/20C07D413/14
Inventor 武永财郭晖郭礼新
Owner CHENGDU GUOHONG PHARMA
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