N-methyl-3 phenyl succinimide compound and preparation method thereof

A technology of phenylsuccinimide and methylmaleimide, applied in directions such as organic chemistry, can solve problems such as unfavorable industrial large-scale production, unfavorable industrialized production, NaH danger, etc., and achieves easy industrialized production and low cost , the effect of shortening the reaction time

Inactive Publication Date: 2015-04-08
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Among the above four synthetic methods, the catalyst required for method one is more expensive and the use of NaH in the reaction is more dangerous, which is not conducive to industrial production
The rhodium catalyst used in method two is relatively expensive, the reaction route in method three is relatively long and there are more by-products produced, and the three wastes in method four are more serious
are not conducive to large-scale industrial production

Method used

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  • N-methyl-3 phenyl succinimide compound and preparation method thereof
  • N-methyl-3 phenyl succinimide compound and preparation method thereof
  • N-methyl-3 phenyl succinimide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 46.5g (0.5mol) of aniline, 250mL of water, 220g of 40% fluoroboric acid aqueous solution, and add dropwise a solution of 36.5g (0.55mol) of sodium nitrite and 100mL of water under stirring at 0 to 5°C. After reacting for 2 hours, suction filtration was completed to obtain 80.6 g of white phenylfluoroborate diazonium salt with a yield of 84.0%, which was directly used in the next reaction.

Embodiment 2

[0039] Add 46.5g (0.5mol) of aniline, 200mL of water, and 300g of 40% fluoroboric acid aqueous solution, and add dropwise a solution of 36.5g (0.55mol) of sodium nitrite and 100mL of water at 0-5°C with stirring, and continue to stir at room temperature. After reacting for 2 hours, suction filtration was completed to obtain 85.0 g of white phenylfluoroborate diazonium salt with a yield of 88.5%, which was directly used in the next reaction.

Embodiment 3

[0041] Take 55.5g (0.5mol) of N-methylmaleimide, 565g (0.55mol) of 15% titanium trichloride aqueous solution and 140g (1.76mol) of sodium acetate, add 280mL of acetone, and stir in batches at -15°C Add 115.2 g (0.6 mol) of phenyltetrafluoroborate diazonium salt, and complete the addition in 2 hours. After the addition is completed, stir at -15°C for 1 hour, then slowly rise to room temperature and stir for 6 hours. After the reaction was completed, evaporate acetone, add ethyl acetate 1000mL for extraction, wash with water, dry the ethyl acetate layer with anhydrous sodium sulfate, evaporate the solvent, and recrystallize from ethanol to obtain 70.5g of white crystals, with a yield of about 74.6%, mp: 72~ 73°C.

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Abstract

The invention relates to an N-methyl-3 phenyl succinimide compound and a preparation method thereof. The structural formula of the compound is: the formula is described in the description. The preparation method comprises the following steps: with aniline as a raw material, reacting aniline with fluoboric acid and sodium nitrite at 5 DEG C to prepare a phenyl fluoroborate diazonium salt; reacting the phenyl fluoroborate diazonium salt with N-methylmaleimide in the presence of titanium trichloride with acetone / water as a solvent at minus 15 to 25 DEG C to obtain the N-methyl-3 phenyl succinimide compound. The yield of the N-methyl-3 phenyl succinimide compound prepared in the invention is high, the raw material is cheap and is easy to obtain, the reaction operation is simple, the reaction route is short, three wastes are few, and industrial production is easy to achieve.

Description

technical field [0001] The invention belongs to the field of phenylsuccinyl compounds and their preparation, in particular to an N-methyl-3-phenylsuccinimide compound and a preparation method thereof. Background technique [0002] Phensuximide (Phensuximide) chemically named N-methyl-3-phenylsuccinimide (1) is a succinimide compound for the treatment of epileptic seizures, commonly used for epileptic seizures and psychomotor disorders Onset, oral administration: 0.5g each time, 2-3 times a day. For children, 20-50 mg per kilogram of body weight per day, divided into 2-3 times, starting with a small dose, and increasing to a sufficient amount in 3-4 weeks. (Kesselheim, A.S.; Stedman, M.R.; Bubrick, E.J.; Gagne, J.J.; Misono, A.S.; Lee, J.L.; Brookhart, M.A.; Avorn, J.; Shrank, W.H. Drugs, 2010, 70(5):605-621; Lapszewicz, J.; Lange, J.; Rump, S.; Walczyna, K.. European Journal of Medicinal Chemistry, 1978,13(5):465-8.; Tracy, G.; Blaise, B.;, Avital , C.; David, C.; Carlos,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/408
CPCC07D207/408
Inventor 赵圣印陈中辉
Owner DONGHUA UNIV
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