501-68-8

Basic information

• Product Name: Beclamide
• Synonyms: Beclamide;Hibicon;Neuracen;Nidrane;Posedrine;3-chloro-N-(phenylmethyl)propanamide;BeklaMid;Chlorakon
• CAS NO: 501-68-8
• Molecular Formula: C₁₀H₁₂ClNO
• Molecular Weight: 197.664
• EINECS: 207-927-1
• Product Categories: NEURACEN
• Mol File: 501-68-8.mol
• Article Data: 9

Chemical Properties

• Melting Point: 94°
• Boiling Point: 386.9°Cat760mmHg
• Flash Point: 187.8°C
• Appearance: /
• Density: 1.1363 (rough estimate)
• Vapor Pressure: 3.42E-06mmHg at 25°C
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.55±0.46(Predicted)
• CAS DataBase Reference: Beclamide(CAS DataBase Reference)
• NIST Chemistry Reference: Beclamide(501-68-8)
• EPA Substance Registry System: Beclamide(501-68-8)

Safety Data

• Hazardous Substances Data: 501-68-8(Hazardous Substances Data)

Usage

Originator

Posedrine,Biosa,Switz.

Uses

Different sources of media describe the Uses of 501-68-8 differently. You can refer to the following data:
1. Beclamide is a chlorinated benzylpropanamide used as an anticonvulsant drug. It is used in the treatment of tonic-clonic seizyres and has sedative properties.
2. anticonvulsant, antiepileptic

Manufacturing Process

A 100 gallon lined jacketed kettle provided with cooling is charged with 100 lb of benzylamine and 150 liters of water. The mixture is cooled to 5°C and with stirring 119 lb of β-chloropropionyl chloride and a solution of 45 lb of sodium hydroxide pellets in 40 liters of water are added simultaneously at such a rate that the temperature does not exceed 10°C. During this period the pH of the mixture should be on the alkaline side but below pH 9.5. When the addition is complete the pH should be about 8. The mixture is stirred overnight in the cold, and the solid product is filtered. The filter cake is reslurred with about 80 gallons of water, filtered, and air-dried. Yield, 128 pounds. The crude material is recrystallized by dissolving it in the minimal quantity of hot methanol (about 50 gallons), adding Norite, and filtering hot. Upon cooling slowly (finally to about 5°C) large crystals separate: they are filtered and air-dried. Yield, 109 pounds. Melting point 92° to 93°C.

Therapeutic Function

Anticonvulsant

Safety Profile

Moderately toxic by ingestion,intraperitoneal and intravenous routes. When heated todecomposition it emits very toxic fumes of Cl- and NOx.An anticonvulsant.

InChI:InChI=1/C10H12ClNO/c11-7-6-10(13)12-8-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)

Upstream product

• 625-36-5 2-chloropropionyl chloride 
• 100-46-9 benzylamine 
• 107-94-8 chloropropionic acid 
• 79-10-7 acrylic acid 

Downstream Products

• 14348-33-5 N-Benzyl-3-carbamimidoylsulfanyl-propionamide 
• 1233488-33-9 C₁₂H₁₄N₄OS 
• 482637-74-1 N-benzyl-2-(4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-ylthio)acetamide 
• 1110930-72-7 C₁₂H₁₄N₄O 
• 1185560-38-6 C₁₃H₁₅N₃O 
• 4458-64-4 N-benzyl-2-azetidinone 
• 100861-67-4 N,N-diethyl-β-alanine benzylamide 
• 13304-62-6 N-benzylacrylamide 

Relevant articles and documents

Atom- and Mass-economical Continuous Flow Production of 3-Chloropropionyl Chloride and its Subsequent Amidation

3-Chloropropionyl chloride is a chemically versatile building block with applications in the field of adhesives, pharmaceuticals, herbicides and fungicides. Its current production entails problems concerning safety, prolonged reaction times and the use of excessive amounts of chlorinating reagents. We developed a continuous flow procedure for acid chloride formation from acrylic acid and a consecutive 1,4-addition of hydrogen chloride generating 3-chloropropionyl chloride, as presented in this paper. Up to 94 % conversion was reached in 25 minutes at mild temperatures and pressures. This continuous flow method offers a safer alternative and is highly efficient in terms of consumption of starting product and shorter residence time. Valorization of this building block is exemplified by the synthesis of beclamide, a compound with sedative and anticonvulsant properties. Over 80 % conversion towards this drug was achieved in 1 minute in a continuous flow setup. Further research is needed to telescope the synthesis of 3-chloropropionyl chloride and subsequent beclamide formation without intermediate purification.

In silico and experimental identification of non ulcerogenic antiinflammatory agents: 3-Thio substituted-4,5-diaryl-4H-1,2,4-triazoles

A new series of 4,5 diaryl-1,2,4-triazole-3-thione substituted carboxamides have been designed, synthesized and tested for their analgesic and antiinflammatory potential. All the tested compounds exhibit antiinflammatory activity comparable to that of standard drugs rofecoxib and diclofenac. Some compounds demonstrate significant analgesic activity in contrast to reference drugs. Compound 9c has emerged as a highly potent lead compound. Ulcerogenic studies of synthesized compounds and rofecoxib show nil or negligible ulcerogenic effect compared to diclofenac. In silico analysis (docking studies) of the most active compound 9c has revealed hypothetical binding mode of the target compound to the cyclooxygenase isoenzyme (COX-2). Docking study has anticipated stereoselective binding mode for the most active compound 9c.

Synthesis and biological screening of novel derivatives of 3-(N-substituted carboxamidoethylthio)-(4H)-1,2,4-triazoles

3-Mercapto-(4H)-1,2,4-triazole has been synthesized from 1-formylthiosemicarbazide. Different N-substituted β-chloropropionamides have been prepared by reacting substituted amines with β- chloropropionylchloride. Different Nsubstituted β-chloropropionamides have been condensed with 3-mercapto-(4H)-1,2,4-triazole in basic medium to obtain various 3-(N-substituted carboxamidoethylthio)-(4H)-1,2,4-triazoles. The structure of the synthesized compounds are confirmed by IR, 1H NMR spectra and elemental analysis. All the compounds have been screened for their analgesic, anti-inflammatory and anxiolytic activity.