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Novel preparation method of 5-iodine-2-phenyl-1-methyl imidazole

A technology of methylimidazole and phenylimidazole, applied in the field of preparation of pharmaceutical chemicals, can solve the problems of raw material waste and low quantity

Inactive Publication Date: 2016-07-20
SOUTHWEAT UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Due to reasons such as steric hindrance, the amount obtained by 5-iodo-2-phenyl-1-methylimidazole is often low (4-iodo: 5-iodine=5:3, the productive rate of 5-iodoimidazole is based on 4-iodo -1H imidazole is only more than 30% at the beginning), if only 5-iodo-2-phenyl-1-methylimidazole is needed, the waste of raw materials is extremely serious, so it is necessary to find a high-yield, easy-to-handle method appear particularly important

Method used

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Examples

Experimental program
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Effect test

Embodiment 14

[0012] Example 14-iodo-2-phenyl-1-p-toluenesulfonyl-1H-imidazole (4)

[0013] Dissolve 4-iodoimidazole in tetrahydrofuran, add potassium hydride solution, stir at room temperature for 30 minutes, then slowly add p-toluenesulfonyl chloride, heat up to reflux after addition, and react until the raw materials are completely reacted after 4 hours. After stopping the reaction, remove tetrahydrofuran, add mL of water and extract with ethyl acetate (3*100mL), combine the organic phases, remove the solvent in vacuo, and recrystallize to obtain 4-iodo-2-phenyl-1-p-toluenesulfonyl-1H - imidazole, yield 91%.

[0014] LC-MS: m / z=425(M+1).

[0015] 1 HNMR (600MHz, DMSO-d 6 ):δ7.71(s,1H),7.44-7.47(m,1H),7.33-7.37(m,5H),7.27(s,1H),7.13-7.14(m,2H),2.38(s,3H ).

Embodiment 24

[0016] Example 24-iodo-3-methyl-2-phenyl-1-p-toluenesulfonyl-1H-imidazolium iodide (5)

[0017] Place 4-iodo-2-phenyl-1-p-toluenesulfonyl-1H-imidazole in toluene, add 1.5 equivalents of methyl iodide (or dimethyl sulfate), remove the toluene after the mixed solution is refluxed for 3 hours, and obtain The yellow muddy substance was stirred and dispersed with petroleum ether (3*20mL) to remove excess iodomethane, and finally the yellow gum was collected and dried, and used directly for the next reaction.

Embodiment 35

[0018] Example 35-iodo-2-phenyl-1-methylimidazole (3)

[0019] The yellow gum (g, 50.0mmol) obtained in the previous step reaction was dissolved in 200mL of 50% aqueous acetic acid solution, and refluxed overnight. Stop the reaction after monitoring the completion of the reaction by pointing the plate, cool to room temperature, filter to obtain the suspension, and wash with 50% acetic acid aqueous solution. The solid was dried and dissolved in dichloromethane and adjusted to pH 10-11 with 1N sodium hydroxide solution. The organic phase was separated and the aqueous phase was extracted with dichloromethane (3*150 mL). The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed in vacuo to obtain a white solid with a yield (total of the last two steps) of 78%.

[0020] LC-MS: m / z=285 (M+1).

[0021] 1 HNMR (600MHz, DMSO-d 6 ): δ7.55-7.56 (m, 2H), 7.43-7.50 (m, 4H), 3.72 (s, 3H).

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Abstract

The invention discloses a novel preparation method of 5-iodine-2-phenyl-1-methyl imidazole.The method comprises the three reaction steps of 1H substitution (upper leaving group), imidazolium salt preparation and leaving group removal conducted on 4-iodine-2-phenyl imidazole.The novel preparation method has the advantages of being high in yield and simple and convenient to operate and making a final product easy to separate.

Description

technical field [0001] The invention relates to a preparation method of medicinal chemicals, in particular to a preparation method of 5-iodo-2-phenyl-1-methylimidazole. Background technique [0002] 5-iodo-2-phenyl-1-methylimidazole is an important pharmaceutical and chemical intermediate, which can be used to synthesize highly functional ionic compounds with antibacterial activity, and can synthesize molecules with light-modulated ionic interactions. It can synthesize Phosphatidylinositol3-kinase (PI3K) inhibitor, can synthesize a model that simulates non-heme metalloenzyme, and can synthesize a valuable pharmaceutically active compound that inhibits ATP-sensitive potassium ion channels in heart muscle and is suitable for use. An important pharmaceutical and chemical intermediate. [0003] The general method of synthesizing 5-iodo-2-phenyl-1-methylimidazole is to use 4-iodo-2-phenylimidazole and methylating reagents (such as methyl iodide, dimethyl sulfate, dimethyl carbon...

Claims

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Application Information

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IPC IPC(8): C07D233/68
CPCC07D233/68
Inventor 郑仁林李良春黄毅陈红英袁小红
Owner SOUTHWEAT UNIV OF SCI & TECH
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