Chlorpropamide

Base Information

• Chemical Name: Chlorpropamide
• CAS No.: 94-20-2
• Molecular Formula: C10H13ClN2O3S
• Molecular Weight: 276.744
• Hs Code.: 29350090
• European Community (EC) Number: 202-314-5
• NSC Number: 756690,626720,44634
• UNII: WTM2C3IL2X
• DSSTox Substance ID: DTXSID9020322
• Nikkaji Number: J3.944F
• Wikipedia: Chlorpropamide
• Wikidata: Q1075324
• NCI Thesaurus Code: C47447
• Pharos Ligand ID: CN6G8TSP674K
• Metabolomics Workbench ID: 42987
• ChEMBL ID: CHEMBL498
• Mol file: 94-20-2.mol

Synonyms:Apo-Chlorpropamide;Chlorpropamide;Clorpropamid;Diabinese;Glucamide;Insogen;Meldian

Chemical Property of Chlorpropamide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 128 °C
• Refractive Index: 1.6300 (estimate)
• Boiling Point: 302°C (rough estimate)
• PKA: pKa 4.8 (Uncertain)
• PSA: 83.65000
• Density: 1.334 g/cm³
• LogP: 3.60050
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: Soluble in ethanol (1:12), acetone (1:5), chloroform (1:9) and solutions of alkali hydroxides. Does not mix well with water.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 276.0335411
• Heavy Atom Count: 17
• Complexity: 345

Purity/Quality:

99% ^*data from raw suppliers

Chlorpropamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCNC(=O)NS(=O)(=O)C1=CC=C(C=C1)Cl
• Recent ClinicalTrials: Study of the Pathogenesis and Pathophysiology of Familial Neurohypophyseal Diabetes Insipidus
• Uses: Chlorpropamide is a sulfonylurea derivative. Chlorpropamide is a long acting hyopglycemic agent. Chlorpropamide is used in the treatment of diabetes metilus type 2. Chlorpropamide acts to increase the secretion of insulin and is not effective in patients who do not have pancreatic beta cell function. For treatment of NIDDM in conjunction with diet and exercise.

Technology Process of Chlorpropamide

There total 7 articles about Chlorpropamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

4-Chlorobenzenesulfonamide (98-64-6) + phenyl N-(n-propyl)carbamate (14549-38-3) → chlorpropamide (94-20-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; acetonitrile; at 80 ℃; for 8h; Flow reactor; Large scale;

DOI:10.1055/a-1664-2282

Reference yield: 94.0%

propylamine (107-10-8,42939-71-9) + 4-Chlorobenzenesulfonamide (98-64-6) + phenyl chloroformate (1885-14-9) → chlorpropamide (94-20-2)

Guidance literature:

propylamine; phenyl chloroformate; With tributyl-amine; In chloroform; at 0 ℃; for 0.00833333h; Flow reactor; Large scale;

4-Chlorobenzenesulfonamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In chloroform; acetonitrile; at 80 ℃; for 8h; Reagent/catalyst; Flow reactor; Large scale;

DOI:10.1055/a-1664-2282

Reference yield: 92.0%

Propyl isocyanate (110-78-1) + 4-Chlorobenzenesulfonamide (98-64-6) → chlorpropamide (94-20-2)

Guidance literature:

With copper(l) chloride; In nitromethane; at 20 ℃; for 2h; Milling;

DOI:10.1039/c3cc47905f

upstream raw materials:

Propyl isocyanate

4-Chlorobenzenesulfonamide

S-Methyl N-propyl(thiocarbamate)

[1,3]-dioxolan-2-one

Downstream raw materials:

n-propylacetamide

N-((4-chlorophenyl)sulfonyl)acetamide

4-Chlorophenylsulfonyl isocyanate

Propyl isocyanate

Refernces

• 1、 Tanwar, Dinesh Kumar,Ratan, Anjali,Gill, Manjinder Singh. "A facile synthesis of sulfonylureas: Via water assisted preparation of carbamates". . p. 4992 - 4999. Retrieved 2017/07/11.
• 2、 Mizuno, Takumi,Kino, Takanobu,Ito, Takatoshi,Miyata, Toshiyuki. "Synthesis of sulfonylurea derivatives used as oral antidiabetics by the selenium-assisted carbonylation using carbon monoxide with sulfur". . p. 3081 - 3089. Retrieved 2007/10/03.