Method for preparing N-methyl phthalimide compound

A technology of methyl phthalimide and phthalimide, which is applied in the field of preparation of N-methyl phthalimide compounds, can solve problems such as pressurization equipment and the like, and achieve reaction The effect of short time, low production cost and high yield

Inactive Publication Date: 2009-02-04
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although in 1997, Notari M etc. disclosed a kind of using dimethyl carbonate as a methylating agent in the form of a patent, methanol as a solvent, methylated phthalimide under the action of potassium carbonate, and synthesized N- Compounds such as methyl phthalimide, but the reaction needs to be carried out at a high temperature of 170 ° C and a relatively high pressure, and it needs disadvantages such as pressurized equipment [Notari, M.; Mizia, F.; Rivetti, F.EP 785189, 1997 [Chem.Abstr.1997, 127:176340]]

Method used

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  • Method for preparing N-methyl phthalimide compound
  • Method for preparing N-methyl phthalimide compound
  • Method for preparing N-methyl phthalimide compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] In the reaction flask, add 73.5 grams (0.5 moles) of phthalimide, 2.85 grams (25 mmoles) of 1,4-diazabicyclo[2.2.2] octane (DABCO), dimethyl carbonate 500 milliliters of esters were stirred and refluxed for reaction, followed by TLC (thin layer chromatography) until the raw material point disappeared, and it took about 7 hours. After the reaction was completed, dimethyl carbonate was distilled off under reduced pressure, 400 ml of water was added, stirred for 10 minutes, and a white solid was obtained by filtration, which was recrystallized with ethanol to obtain 72.8 g of white crystals with a melting point of 132-134°C. The amount of feeding amount and the amount of N-methylphthalimide obtained, the calculated yield is 91%.

[0030] The properties of N-methylphthalimide are as follows:

[0031] IR(KBr)υ: 3105, 2978, 1716, 1609, 1466, 1383, 1292, 1251, 1187, 1156, 1088, 1008cm -1 , 3105cm in the infrared IR spectrum -1 Nearby are the C-H stretching vibra...

Embodiment 2

[0034]

[0035] In the reaction flask, add 73.5 grams (0.5 moles) of phthalimide, 2.85 grams (25 mmoles) of 1,4-diazabicyclo[2.2.2] octane (DABCO), dimethyl carbonate 50 ml of ester and 250 ml of dimethylformamide (DMF) were stirred and refluxed at 110° C., followed by TLC (thin-layer chromatography) until the starting point disappeared, and it took about 5 hours. After the reaction was completed, the dimethyl carbonate was distilled off under reduced pressure, 300 ml of water was added, and extracted with ethyl acetate (200 ml×3). Ethyl acetate was distilled off, and the residue was recrystallized with ethanol to obtain 71.3 g of white crystals with a melting point of 132-134°C. amount, the calculated yield was 89%.

Embodiment 3

[0037]

[0038] Except that 1,4-diazabicyclo[2.2.2]octane (DABCO) in Example 1 was replaced with tetramethylethylenediamine, all the other raw materials, formulations, processes and operating procedures were the same as in Example 1. Obtain 68.4 grams of white N-methylphthalimide crystals, according to the amount of phthalimide charging and the amount of N-methylphthalimide obtained, the calculated yield is 85 %.

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Abstract

The invention relates to a preparation method for N-methyl phthalimide compound, which is a synthetic method for preparing N-methyl phthalimide compound under the action of tertiary amine as catalyst by using phthalimide compound as raw material and dimethyl carbonate as a methylating agent. The preparation method has the advantages of simple operation, low toxicity and little environment pollution, which is applied to industrial production. Meanwhile, the obtained product is high in yield with purity being more than 98 percent.

Description

technical field [0001] The invention belongs to the field of compounds with imide structure, in particular to a preparation method of N-methylphthalimide compound. Background technique [0002] The N- or O-methylation reaction is of great significance in organic synthesis. The N-methylphthalimide obtained by N-methylation of compounds with imide structure such as phthalimide Formimide derivatives are a class of important chemical intermediates, such as N-methylphthalimide can be used to synthesize important intermediates such as drugs, pesticides and chemiluminescent immunoassay reagents [Neumann, H.; Struebing , D.; Lalk, M.; et.al.Org.Biomol.Chem.2006, 4(7):1365-1375; Oh, S.W.; Kim, J.Y.; Cho, D.W.et.al.Bull.Korean Chem. Soc.2007, 28(4):629-634]. At present, the method for preparing N-methylphthalimide mainly contains the reaction preparation of phthalic anhydride and methylamine [Zheng Kai, Yao Cheng. Petrochemical Industry, 2004, 33 (2): 145-148] and N-methylation wit...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
Inventor 赵圣印卿凤翎邵志宇张海泉
Owner DONGHUA UNIV
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