Vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, preparation method thereof as well as method for preparing vitamin B6

A technology for alkylsiloxy oxazole and vitamin, which is applied in the field of chemical synthesis of vitamin B6, can solve the problems of complicated preparation process, unfavorable environmental protection and high price of oxazole, and achieves high reaction selectivity, convenient source of raw materials and low cost. Effect

Active Publication Date: 2015-06-03
XINFA PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Its disadvantages are that the price of raw material 4-methyl-5-alkoxy-oxazole is relatively high, the preparation proc

Method used

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  • Vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, preparation method thereof as well as method for preparing vitamin B6
  • Vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, preparation method thereof as well as method for preparing vitamin B6
  • Vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, preparation method thereof as well as method for preparing vitamin B6

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the preparation of 4-methyl-5-trimethylsiloxy oxazole

[0050] Step 1: Preparation of 4-methyltetrahydrothiazol-5-one

[0051] Add 89.0 grams (1.0 moles) of 2-aminopropionic acid, 2.0 grams of p-toluenesulfonic acid and 800 grams of Toluene, after heating up to 110°C and refluxing, add 105 grams (1.3 moles) of 37% formaldehyde solution dropwise for about 3 hours, then reflux for 5 hours for dehydration to obtain a toluene solution of 4-methyltetrahydrothiazol-5-one , used directly in step 2.

[0052] Step 2: Preparation of 4-methyl-5-trimethylsilyloxyoxazole

[0053] The toluene solution of 4-methyltetrahydrothiazol-5-one obtained in step 1 is cooled to 10° C., 440 grams (3.2 moles) of potassium carbonate are added, and 75 grams (1.06 moles) of chlorine gas is introduced between 10 and 15° C. After passing through, react at 10-15°C for 4 hours. Then, 120 g (1.1 moles) of trimethylchlorosilane was added dropwise at 10-15° C., and the reaction was carrie...

Embodiment 2

[0054] Embodiment 2: the preparation of 4-methyl-5-trimethylsiloxy oxazole

[0055] Step 1: Preparation of 4-methyltetrahydrothiazol-5-one

[0056] Add 89.0 grams (1.0 moles) of 2-aminopropionic acid, 2.0 grams of p-toluenesulfonic acid, and 400 grams of 2-Methyltetrahydrofuran, 400 grams of toluene, and 33 grams (1.1 moles) of paraformaldehyde were heated to 80-85° C. for reflux dehydration reaction for 5 hours. Cool to obtain a toluene solution of 4-methyltetrahydrothiazol-5-one, which is directly used in step 2.

[0057] Step 2: Preparation of 4-methyl-5-trimethylsilyloxyoxazole

[0058] Cool the toluene solution of 4-methyltetrahydrothiazol-5-one obtained in step 1 to 10°C, add 245 grams (3.1 moles) of pyridine, and feed 75 grams (1.06 moles) of chlorine gas between 10 and 15°C. After completion, react at 10-15°C for 4 hours. Then, 120 g (1.1 moles) of trimethylchlorosilane was added dropwise at 10-15° C., and the reaction was carried out at 10-15° C. for 3 hours. Rem...

Embodiment 3

[0059] Embodiment 3: the preparation of 4-methyl-5-trimethylsiloxy oxazole

[0060] Step 1: Preparation of 4-methyltetrahydrothiazol-5-one

[0061] Add 89.0 grams (1.0 moles) of 2-aminopropionic acid, 1.8 grams of benzenesulfonic acid and 800 grams of toluene to a 2000 mL four-necked flask equipped with stirring, a thermometer, a constant pressure dropping funnel, a reflux condenser and a water separator, and heat up After refluxing to 110° C., 105 g (1.3 moles) of 37% formaldehyde aqueous solution was added dropwise for about 3 hours, and then refluxed for dehydration for 6 hours. Cool to obtain a toluene solution of 4-methyltetrahydrothiazol-5-one, which is directly used in step 2.

[0062] Step 2: Preparation of 4-methyl-5-trimethylsilyloxyoxazole

[0063] The toluene solution of 4-methyltetrahydrothiazol-5-one obtained in step 1 is transferred to the equipment equipped with stirring, thermometer, constant pressure dropping funnel, reflux condenser and tail gas absorption...

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Abstract

The invention relates to a vitamin B6 intermediate 4-methyl-5-alkylsiloxane oxazole, a preparation method thereof as well as a method for preparing the vitamin B6. 4-methyl-5-alkylsiloxane oxazole has the structure shown as the formula I. 2-alanine and formaldehyde or paraformaldehyde are subjected to N-hydroxymethylation and lactonization in a solvent under the action of an acid catalyst to obtain 4-methyl-tetrahydro-oxazole-5-ketone (II), the ketone is not separated and is directly subjected to chloro substitution, silicon etherification and an elimination reaction in the presence of an acid-binding agent to generate 4-methyl-5-alkylsiloxane oxazole (I). 4-methyl-5-alkylsiloxane oxazole and 2-n-propyl-1,3-dioxo-5-cycloheptene are subjected to addition and hydrolysis to prepare the vitamin B6. The process is short, the operation is easy, little wastewater is produced, safety and environmental protection are realized, the reaction selectivity is good, a product is low in cost and high in purity, and industrial production is facilitated better.

Description

technical field [0001] The invention relates to a vitamin B 6 Intermediate 4-methyl-5-alkylsiloxy oxazole and its convenient preparation method, and preparation of vitamin B by the intermediate 6 method, belonging to vitamin B 6 The field of chemical synthesis technology. Background technique [0002] Vitamin B 6 (Vitamin B 6 , referred to as VB 6 ) is one of the essential vitamins for the human body, plays a key role in the growth of animals, and is widely used in the fields of medicine, food, feed additives and cosmetics industries. Vitamin B 6 It exists in three forms of pyridoxine, pyridoxal and pyridoxamine in nature, and these three forms can be transformed into each other in the body under certain conditions. Industrially synthesized vitamin B 6 It is generally pyridoxine hydrochloride, and vitamin B is usually produced by chemical synthesis 6 , the research and production mostly focus on the improvement of the "oxazole method" synthesis process, in which 4-m...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07D213/67
Inventor 戚聿新吕强三鞠立柱李新发
Owner XINFA PHARMA
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