26750-81-2

Basic information

• Product Name: Alibendol
• Synonyms: hydroxy-2methoxy-3allyl-5n-(beta-hydroxyethyl)benzamide;Alibendol ,2-hydroxy-3-methoxy-5-allyl-N-(C-hydroxyethyl)-benzamide;5-Allyl-2-hydroxy-N-(2-hydroxyethyl)-3-methoxybenzamide;5-Allyl-N-(2-hydroxyethyl)-3-methoxysalicylamide;Cebera;H-3774;PC-54;2-hydroxy-N-(2-hydroxyethyl)-3-methoxy-5-prop-2-enylbenzamide
• CAS NO: 26750-81-2
• Molecular Formula: C₁₃H₁₇NO₄
• Molecular Weight: 251.28
• EINECS: 247-960-9
• Product Categories: Active Pharmaceutical Ingredients;API;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 26750-81-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 97-99°C
• Boiling Point: 402.4 °C at 760 mmHg
• Flash Point: 197.2 °C
• Appearance: Powder
• Density: 1.192 g/cm³
• Vapor Pressure: 3.37E-07mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 8.59±0.48(Predicted)
• Merck: 14,244
• CAS DataBase Reference: Alibendol(CAS DataBase Reference)
• NIST Chemistry Reference: Alibendol(26750-81-2)
• EPA Substance Registry System: Alibendol(26750-81-2)

Safety Data

• RTECS: CU8730000
• Hazardous Substances Data: 26750-81-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Originator

Cebera ,Bouchara ,France ,1981

Uses

Different sources of media describe the Uses of 26750-81-2 differently. You can refer to the following data:
1. Alibendol is an antispasmodic,choleretic, and cholekinetic.
2. An amide analog of Eugenol, and is used therapeutically as an antispasmodic.

Manufacturing Process

36 g of ethyl ester of 2-hydroxy-3-methoxy-5-allyl-benzoic acid [obtained by the process described by Pearl, et al., J. Amer. Chem. Soc., Vol. 71, 1067- 1068 (1949)] and 61 g of ethanolamine were admixed and left to stand for 1 hour at ambient temperature after which it was heated for 1 hour at 120°C. The mixture was extracted with chloroform and the organic phases were washed with half diluted hydrochloric acid, then with water, and the chloroform evaporated off. The residue, after recrystallization from benzene, was a 78% yield of 2-hydroxy-3-methoxy-5-allyl-N-(β-hydroxyethyl)- benzamide having a melting point of 95°C. The product appeared in the form of colorless crystals which were insoluble in water and soluble in dilute sodium hydroxide.

Therapeutic Function

Choleretic, Spasmolytic

InChI:InChI=1/C13H17NO4/c1-3-4-9-7-10(13(17)14-5-6-15)12(16)11(8-9)18-2/h3,7-8,15-16H,1,4-6H2,2H3,(H,14,17)

Upstream product

• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 6342-70-7 3-methoxymethylsalicylate 
• 85614-43-3 2-hydroxy-3-methoxy-5-(2-propeny)benzoic acid, methyl ester 
• 141-43-5 ethanolamine 

Relevant articles and documents

Choleretic drug alibendol preparation method

The invention belongs to the field of drug synthesis, and provides an alibendol preparation method, which comprises: selecting 2-hydroxy-3-methoxybenzaldehyde as a raw material, selecting an efficientoxidative esterification catalyst, carrying out one-step oxidative esterification to obtain methyl 2-hydroxy-3-methoxybenzoate, carrying out a reaction on the methyl 2-hydroxy-3-methoxybenzoate and allyl bromide under the action of an alkali to generate methyl 2-allyloxy-3-methoxybenzoate, carrying out a para Claisen rearrangement reaction on the methyl 2-allyloxy-3-methoxybenzoate at a high temperature to obtain methyl 2-hydroxy-3-methoxy-5-allylbenzoate, and carrying out an aminolysis reaction in ethanolamine to generate alibendol. Compared with the traditional synthetic process, the new process of the present invention has characteristics of simple synthesis steps, convenient post-treatment and good product quality, and is suitable for industrial production.