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Process for preparing 5-[[(3,5-di-tertiary-butyl)-4-hydroxy phenyl] methylene]2-imino-thiazolinone methyl sulfonate

A technology of thiazolinone mesylate and di-tert-butyl, applied to (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl]methylene]-2 -The field of preparation of imino-4-thiazolinone mesylate can solve the problems of complicated preparation method, low total yield and long reaction time, and achieve the effects of shortened reaction time, high yield and simple process

Inactive Publication Date: 2006-11-08
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the above method, (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl]methylene]-2-imino-4-thiazolinone (CI-100

Method used

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  • Process for preparing 5-[[(3,5-di-tertiary-butyl)-4-hydroxy phenyl] methylene]2-imino-thiazolinone methyl sulfonate
  • Process for preparing 5-[[(3,5-di-tertiary-butyl)-4-hydroxy phenyl] methylene]2-imino-thiazolinone methyl sulfonate

Examples

Experimental program
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Embodiment 1

[0032] Example 1: In a dry 500ml round bottom bottle, 3,5-di-tert-butyl-4-hydroxybenzaldehyde 31.5g (0.14mol), thiourea 10.5g (0.14mol), ethyl chloroacetate 16.5g (0.14mol) and newly distilled benzene 400ml, reflux reaction for 14 hours, slowly distill 200ml of benzene-water azeotrope. with 10% NaHCO 3 Wash with aqueous solution until the solution is weakly alkaline, wash with water until neutral, separate the aqueous layer, and wash the organic layer with Na 2 SO 4 dry. decant the upper layer, Na 2 SO 4 Wash with chloroform until colorless. Combine the organic matter, concentrate under reduced pressure until the remaining 50 g of the system is filtered after cooling, and the solid is washed with hot CH 2 Cl 2 0ml is washed and dried to obtain product (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl] methylene]-2-imino-4-thiazolinone (hereinafter referred to as CI-1004) 28.7 g, yield 61.8%.

[0033] Add CI-1004 (0.065mol) and 6.6g (0.068mol) of methanesulfonic acid into 20...

Embodiment 2

[0034] Embodiment 2: As described in Embodiment 1, the difference is that the solvent of the synthesis reaction is chloroform. The yield is the same.

Embodiment 3

[0035] Embodiment 3: in dry 500ml round bottom bottle, 3,5-di-tert-butyl-4-hydroxybenzaldehyde 31.5g (0.14mol), thiourea 10.5g (0.14mol), methyl chloroacetate 15.2g (0.14 mol) and freshly steamed toluene 400ml, reflux reaction for 12 hours, slowly steamed out 200ml of toluene-water azeotrope. with 10% NaHCO 3 Wash with aqueous solution until the solution is weakly alkaline, wash with water until neutral, separate the aqueous layer, and wash the organic layer with Na 2 SO 4 dry. decant the upper layer, Na 2 SO 4 Wash with chloroform until colorless. The organic layers were combined, concentrated under reduced pressure to 50 g left in the system, filtered after cooling, and the solid was washed with hot CH 2 Cl 2 20ml was washed and dried to obtain 31g of product CI-1004 with a yield of 66.7%.

[0036]Add CI-1004 (0.065mol) and 6.6g (0.068mol) of methanesulfonic acid into 200ml of chloroform, and stir overnight at room temperature. After evaporating to dryness in a wate...

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Abstract

The preparation process of (Z)-5-[[(3, 5-di-tertiary butyl)-4-hydroxy phenyl] methylene]-2-imino -4-thiazolinone methyl sulfonate belongs to the field of chemical technology. Haloacetic acid, haloacetyl halide or haloacetate is reacted with 3, 5- di-tertiary butyl -4- hydroxy phenyl formaldehyde and thiourea in the presence or absence of anhydrous sodium acetate; and the obtain product is washed and dried to obtain (Z)-5-[[(3, 5-di-tertiary butyl)-4-hydroxy phenyl] methylene]-2-imino -4-thiazolinone. The product is further reacted with methane sulfonic acid to obtain the end product. The present invention synthesizes the key intermediate with simple industrial material (Z)-5-[[(3, 5-di-tertiary butyl)-4-hydroxy phenyl] methylene]-2-imino -4-thiazolinone, and has simplified operation, high yield and low cost.

Description

(1) Technical field [0001] The present invention relates to non-steroidal anti-inflammatory drug (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl]methylene]-2-imino-4-thiazolinone Process for the preparation of sulfonates. (2) Background technology [0002] Darbufelone, also known as Darbufelone, its English name is Darbufelone, chemical name: methanesulfonic acid (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl]methylene base]-2-imino-4-thiazolinone salt, or (Z)-5-[[(3,5-di-tert-butyl)-4-hydroxyphenyl]methylene]-2-imino -4-thiazolinone methanesulfonate, the structural formula is as follows: [0003] [0004] Dabufeilong is a new type of non-steroidal anti-inflammatory drug developed by Warner-Lambert (Warner-Lambert) Company of the United States for the treatment of rheumatoid arthritis and osteoarthritis. It belongs to thiazolone bis-tert-butylphenol compounds, is a dual inhibitor of 5-lipoxygenase and cyclooxygenase-2, and is a non-ulcerative anti-inflammatory drug. [0005]...

Claims

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Application Information

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IPC IPC(8): C07D277/40
Inventor 林吉茂林振广冯永斌
Owner SHANDONG UNIV