Synthesis method for 4-methyl-5-(2-ethoxyl)-thiazole

A synthesis method and hydroxyethyl technology, applied in the direction of organic chemistry, etc., can solve the problems of many reaction steps, large amount of three wastes, low yield, etc., and achieve the effect of reducing reaction steps, low toxicity and high yield

Active Publication Date: 2012-07-18
WUTONG AROMA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many reaction steps, low yield, large amount of three wastes

Method used

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  • Synthesis method for 4-methyl-5-(2-ethoxyl)-thiazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] 1) Ammonification:

[0039] Introduce ammonia into carbon disulfide to obtain ammonium salt; carbon disulfide: ammonia = 1:1.2, molar ratio; reaction temperature: 15°C;

[0040] 2) Chlorination:

[0041] In a 500ml four-neck flask equipped with a stirrer and a temperature measuring device, add 0.2mol of α-acetyl-γ-butyrolactone, add CaCl 2 and NaHPO 4 125ml of mixed solution; NaHPO 4 The concentration is 0.5mol / L; CaCl 2 : NaHPO 4 =1:1, molar ratio; then pass chlorine gas under the irradiation of ultraviolet light, hydrolyze to get 3-chloroacetylpropanol; 2-acetylbutyrolactone: chlorine gas=1:1, molar ratio; reaction time 1.5 hours, The reaction temperature is 15°C; more preferably, ultraviolet light with a wavelength of 200nm is used;

[0042] 3) Condensation:

[0043] The 3-chloroacetylpropanol obtained in step 2) is condensed with the ammonium salt obtained in step 1) to obtain a condensate; the ratio of 3-chloroacetylpropanol to the ammonium salt obtained in ...

Embodiment 2

[0049] 1) Ammonification:

[0050] Introduce ammonia into carbon disulfide to obtain ammonium salt; carbon disulfide: ammonia = 1:1.1, molar ratio; reaction temperature: 10°C;

[0051] 2) Chlorination:

[0052] In a 500ml four-neck flask equipped with a stirrer and a temperature measuring device, add 0.2mol of α-acetyl-γ-butyrolactone, add CaCl 2 and NaHPO 4 125ml of mixed solution; NaHPO 4 The concentration is 1.2mol / L; CaCl 2 : NaHPO 4 =1:1, molar ratio; then pass chlorine gas under the irradiation of ultraviolet light, hydrolyze to get 3-chloroacetylpropanol; 2-acetylbutyrolactone: chlorine gas=1:0.8, molar ratio; reaction time is 2 hours, The reaction temperature is 10°C; use ultraviolet light with a wavelength of 250nm;

[0053] 3) Condensation:

[0054] The 3-chloroacetylpropanol obtained in step 2) is condensed with the ammonium salt obtained in step 1) to obtain a condensate; the ratio of 3-chloroacetylpropanol to the ammonium salt obtained in step 1) is 1: 4, m...

Embodiment 3

[0059] 1) Ammonification:

[0060] Introduce ammonia into carbon disulfide to obtain ammonium salt; carbon disulfide: ammonia = 1: 1.5, molar ratio; reaction temperature: 20°C;

[0061] 2) Chlorination:

[0062] In a 500ml four-neck flask equipped with a stirrer and a temperature measuring device, add 0.2mol of α-acetyl-γ-butyrolactone, add CaCl 2 and NaHPO 4 125ml of mixed solution; NaHPO 4 The concentration is 1.0mol / L; CaCl 2 : NaHPO 4 =1:0.9, molar ratio; then pass chlorine gas under the irradiation of ultraviolet light, hydrolyze to get 3-chloroacetylpropanol; 2-acetylbutyrolactone: chlorine gas=1:0.8, molar ratio; reaction time 1.5 hours, The reaction temperature is 20°C; more preferably, ultraviolet light with a wavelength of 300nm is used;

[0063] 3) Condensation:

[0064] The 3-chloroacetylpropanol obtained in step 2) is condensed with the ammonium salt obtained in step 1) to obtain a condensate; the ratio of 3-chloroacetylpropanol to the ammonium salt obtaine...

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Abstract

The invention provides a preparation method for 4-methyl-5-(2-ethoxyl)-thiazole. The 4-methyl-5-(2-ethoxyl)-thiazole is synthesized from 2-acetylbutyrolactone serving as a raw material through amination, chloration, condensation and oxidative reaction. The preparation method comprises the following steps of: introducing chlorine into 2-acetylbutyrolactone and hydrolyzing to obtain 3-acetyl chloride propyl alcohol; introducing ammonia gas into carbon bisulfide to obtain ammonium salt; oxidizing a condensation product of 3-acetyl chloride propyl alcohol and the ammonium salt with hydrogen peroxide or oxygen to obtain a product; extracting with dichloromethane; removing the dichloromethane; then performing reduced pressure distillation; and collecting fraction at 120-127 DEG C under the pressure of 395-400 Pa. The synthesis method has the advantages of readily available raw material, low production cost, simple process, mild reaction conditions and yield of reaching up to 82 percent.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a synthesis process of 4-methyl-5-(2-hydroxyethyl)-thiazole. Background technique [0002] Thiazole, the chemical name is: 4-methyl-5-(β-hydroxyethyl)-thiazole, 4-methyl-5-(2-hydroxyethyl)-thiazole, CAS: 137-00-8, English name : 4-Methyl-5-beta-hydroxyethyl thiazole referred to as MHT, boiling point: 135 ℃ / 933.3Pa, 123 ~ 124 ℃ / 399.9Pa, 103 ℃ / 133.3Pa. Refractive index: nD20 =1.5470, light yellow to brown yellow transparent liquid. Non-volatile; non-flammable, non-explosive; non-corrosive; non-toxic. Its structural formula is shown in the appendix of the manual figure 1 . [0003] Thiazole is a component of vitamin VB 1 The basic structural ring of VB1 is also an important intermediate for the synthesis of VB1. At the same time, it is also a precious spice. It has a nutty, bean, milky, eggy, and meaty aroma, so it is used in nuts, milky meat and seasoning flavors. 4-M...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/24
Inventor 卫洁孙斌李新王立志宋成斌郗金标张知伟张成果卢朋张雷亮高敬怀李晟
Owner WUTONG AROMA CHEM CO LTD
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