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Preparation method of N-alkyl phthalimide compound

A technology of alkyl phthalimide and phthalic anhydride, applied in the field of preparation of N-alkyl phthalimide compounds, can solve the problem of high cost of methyl iodide and dimethyl carbonate, etc. problem, to achieve the effect of low cost, easy processing and wide range of sources

Inactive Publication Date: 2015-05-13
JINGZHOU TIANHE SCI TECH CHEM IND
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Preparation method of N-alkyl phthalimide compound

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Embodiment 1

[0024] Add 30.0 g (0.203 mol) of phthalic anhydride, 60 g of glacial acetic acid and 2 g of acetic anhydride into the reaction flask, stir and heat to 60°C, keep warm for 20 minutes to partially dissolve the phthalic anhydride, then add 25.0 g (0.242 mol) of 30% methylamine aqueous solution at one time , heated to 130°C for 15 minutes and refluxed for 5 hours. Phthalic anhydride gradually dissolved during the process, and finally a colorless transparent solution was obtained. The product solution was concentrated to 60 g by distillation under reduced pressure, cooled to room temperature and allowed to stand overnight, and a large amount of needle-shaped white solid was precipitated. Suction filtration under reduced pressure and wash the filter cake with a small amount of acetic acid, and dry under reduced pressure at 100°C to obtain 26.7 g of white needle-like N-methylphthalimide, with a yield (calculated as phthalic anhydride) of 81.8%.

[0025] Melting point: 129.5-130.4°C....

Embodiment 2

[0030] Add 91.2 grams (0.5 mol) of 4-chlorophthalic anhydride and 200 grams of glacial acetic acid into a three-necked flask, stir and heat to 50°C for 15 minutes, and the 4-chlorophthalic anhydride is completely dissolved. Then, 67.1 g (0.65 mol) of 30% methylamine aqueous solution was added directly, and the temperature was raised to 120°C for 20 minutes to react for 5 hours. After the reaction was completed, it was naturally cooled to room temperature, and a large number of needle-like white crystals were precipitated overnight, filtered under reduced pressure and rinsed with a small amount of glacial acetic acid, and the filter cake was dried under reduced pressure to obtain white granular solid N-methyl-4-chloro-o-phthalic acid Dicarboximide (4-CPI) 78.2 grams, yield 80.2% (calculated as 4-chlorophthalic anhydride)

[0031] Melting point: 135.5-136.2°C

[0032] 1 H NMR (400MHZ DMSO-D 6 ) δ=7.92-7.91(t, J=1.2 Hz, 1H, Ph-H) 7.86(d, J=1.2 Hz, 2H, Ph-H) 3.05(s, 3H, CH 3 ) ...

Embodiment 3

[0038] Add 70.0 g of 3-nitrophthalic anhydride (0.752 mol) into 350 g of glacial acetic acid, stir and heat up to 50°C for 30 minutes, and the 3-nitrophthalic anhydride is partially dissolved. Add 93.2 g (0.902 mol) of 30% methylamine aqueous solution, then gradually dissolve the solid, heat up to 120°C in 15 minutes, and then reflux for 3 hours. The solution was concentrated under reduced pressure to 100 g, cooled naturally, and a large number of needle-shaped yellow solids were precipitated overnight, filtered under reduced pressure and washed with a small amount of glacial acetic acid, dried under reduced pressure to obtain light yellow blocky solid N-methyl-3-nitrate 55.6 grams of phthalimide (3-NPI), yield 74.6% (based on 3-nitrophthalic anhydride).

[0039] The general structural formula of this compound is expression (6)

[0040]

[0041] Melting point: 111.9-113.2°C

[0042] 1 H NMR (400MHZ DMSO-D 6 ): δ= 8.27-8.25(d, J=8 Hz, 1H, Ph-H) 8.16-8.14(d, J= 8 Hz, 1H, ...

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Abstract

The invention relates to a preparation method of substituted-N-alkyl phthalimide, belonging to the technical field of compounds with a phthalimide structure. According to the preparation method, abundant substituted phthalic anhydride is utilized as a reaction raw material, a low-pollution single-alkyl amine water solution is utilized as an imidization reagent, low-grade carboxylic acid is utilized as a solvent, substituted-N-alkyl phthalimide is prepared by virtue of normal pressure reaction, and high-pollution methylamine and ethylamine gas are not used; the substituted phthalic anhydride is utilized as the raw material, industrial products of the compounds are complete, the source of the raw material is wide, the process is simple, and the cost is low; the reaction solvent can be recycled and reused, the treatment after the reaction is simple, the recrystallization is omitted, the yield can reach 83.t0% at most, and the purity is above 99%.

Description

technical field [0001] The invention relates to a preparation method of an N-alkylphthalimide compound, and belongs to the technical field of compounds with a phthalimide structure. Background technique [0002] N-Alkylphthalimide compounds are a class of important chemical intermediates, such as N-methylphthalimide can be used in drug synthesis, pesticides and chemiluminescent immunoassay reagents [Neumann H, Struebing D, Lalk M, et.al. Synthesis and antimicrobial activity of N-analogous corollasporines [J]. Org. Biomol. Chem. 2006, 4(7):1365-1375]. N-methyl-4-aminophthalimide is an important intermediate for the synthesis of isoluminol derivatives[Schroeder H R, Yeager F M. Chemiluminesc- ence yields and detection limits of some isoluminol derivatives in various oxidation systems [J]. Anal. Chem. 1978, 50(8):1114. Patent, US4302616], there are primary and tertiary amino groups in its molecule, which is sensitive to hydrogen bonding, and can also be used for amphiphile, su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 肖稳发腾飞黄立肖俊涛
Owner JINGZHOU TIANHE SCI TECH CHEM IND
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