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Method for synthesizing O-ethoxy phenyl formamidine acetate

A technology of o-ethoxybenzamidine and ethoxybenzamidine, which is applied in the field of pharmaceutical intermediate synthesis, can solve the problem of high cost and achieve the effects of low cost, simple post-processing and simple process

Inactive Publication Date: 2006-09-13
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] O-ethoxybenzamidine is a new type of drug intermediate, and the above-mentioned synthesis methods 2 and 3 are not applicable, and the cost of the first method is too high

Method used

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  • Method for synthesizing O-ethoxy phenyl formamidine acetate
  • Method for synthesizing O-ethoxy phenyl formamidine acetate
  • Method for synthesizing O-ethoxy phenyl formamidine acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 7.5 grams (0.05mol) of o-ethoxybenzaldehyde, 4.31 grams (0.0575mol) of nitroethane and 6.64 grams (0.0575mol) of anhydrous pyridine hydrochloride in a container, heat to 114 ° C, and reflux for 1 hour , after cooling to room temperature, add 100 ml of chloroform and 100 ml of 0.1M hydrochloric acid solution, mix thoroughly and separate the organic layer, extract the aqueous phase with chloroform 3 times, 20 ml each time, combine the organic phases and wash with water three times, each time 50ml. The product was separated through a silica gel column with a length of 6 cm and a diameter of 2.5 cm and chloroform as eluent to obtain o-ethoxybenzonitrile with a yield of 92%.

[0028] Add 15 ml of ethanol to 5.9 g (0.04 mol) of o-ethoxybenzonitrile, 4.2 g (0.06 mol) of hydroxylamine hydrochloride, and 4.2 g of potassium carbonate, add 15 ml of water in batches under stirring, and heat to 78°C after no bubbles are generated. , refluxed for 3 hours, distilled off ethanol,...

Embodiment 2

[0031] Take 7.5 grams (0.05mol) of o-ethoxybenzaldehyde, 4.31 grams (0.0575mol) of nitroethane and 6.64 grams (0.0575mol) of anhydrous pyridine hydrochloride in a container, heat to 114 ° C, and reflux for 0.5 hours , after cooling to room temperature, add 100 ml of chloroform and 100 ml of 0.1M hydrochloric acid solution, mix thoroughly and separate the organic layer, extract the aqueous phase with chloroform 3 times, 20 ml each time, combine the organic phases and wash with water three times, each time 50ml. The product was separated through a silica gel column with a length of 6 cm and a diameter of 2.5 cm and chloroform as eluent to obtain o-ethoxybenzonitrile with a yield of 92%.

[0032] Add 15 ml of ethanol to 5.9 g (0.04 mol) of o-ethoxybenzonitrile, 4.2 g (0.06 mol) of hydroxylamine hydrochloride, and 4.2 g of potassium carbonate, add 15 ml of water in batches under stirring, and heat to 78°C after no bubbles are generated. , refluxed for 5 hours, distilled off ethan...

Embodiment 3

[0035] Take 7.5 grams (0.05mol) of o-ethoxybenzaldehyde, 4.31 grams (0.0575mol) of nitroethane and 6.64 grams (0.0575mol) of anhydrous pyridine hydrochloride in a container, heat to 114 ° C, and reflux for 2 hours , after cooling to room temperature, add 100 ml of chloroform and 100 ml of 0.1M hydrochloric acid solution, mix thoroughly and separate the organic layer, extract the aqueous phase with chloroform 3 times, 20 ml each time, combine the organic phases and wash with water three times, each time 50ml. The product was separated through a silica gel column with a length of 6 cm and a diameter of 2.5 cm and chloroform as eluent to obtain o-ethoxybenzonitrile with a yield of 92%.

[0036] Add 15 ml of ethanol to 5.9 g (0.04 mol) of o-ethoxybenzonitrile, 4.2 g (0.06 mol) of hydroxylamine hydrochloride, and 4.2 g of potassium carbonate, add 15 ml of water in batches under stirring, and heat to 78°C after no bubbles are generated. , refluxed for 1 hour, distilled off ethanol,...

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Abstract

A process for preparing o-ethoxybenzamidine acetate includes such steps as reflux reaction between o-ethoxy benzaldehyde and nitroethane to obtain o-ethoxy benzonitrile, reflux reacting on hydroxyammonium hydrochloride to obtain o-ethoxy benzamidoxime, and catalytic hydrogenating while stirring.

Description

Technical field: [0001] The invention belongs to the field of synthesis of pharmaceutical intermediates, and relates to a synthesis method of o-ethoxybenzamidine acetate. Background technique: [0002] Studies have found that many natural products contain amidine compounds, which play a very important role in the life process, and aromatic substituted amidines are an important class of pharmaceutical intermediates, so many chemical synthesis methods have been reported. The common synthetic method is to prepare from amides, nitriles and thioamides. Among them, the methods with more market prospects are: [0003] 1. Amides are oxy-alkylated by triethyloxonium fluoroborate at a mild temperature, and react with amines to form amidines. [0004] [0005] 2. Kakimoto reported a synthetic method for the direct conversion of carboxylic acid to amidine using trimethylsilyl polyphosphate (PPSE). [0006] [0007] 3. The Pinner reaction is the most classic method for preparing...

Claims

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Application Information

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IPC IPC(8): C07C257/18
Inventor 石志强马永山袁明鉴邢成芬于莹
Owner SHANDONG NORMAL UNIV
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