Sulfamerazine

Base Information

• Chemical Name: Sulfamerazine
• CAS No.: 127-79-7
• Deprecated CAS: 99482-27-6
• Molecular Formula: C11H12N4O2S
• Molecular Weight: 264.308
• Hs Code.: 2935904000
• European Community (EC) Number: 204-866-2
• NSC Number: 757325,27259
• UNII: UR1SAB295F
• DSSTox Substance ID: DTXSID0023612
• Nikkaji Number: J5.402J
• Wikipedia: Sulfamerazine
• Wikidata: Q415196
• NCI Thesaurus Code: C61959
• Metabolomics Workbench ID: 43575
• ChEMBL ID: CHEMBL438
• Mol file: 127-79-7.mol

Synonyms:Mebacid;Methylsulfadiazine;Sulfamerazine;Trimetox

Chemical Property of Sulfamerazine

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 7.03E-11mmHg at 25°C
• Melting Point: 234-238 °C
• Refractive Index: 1.66
• Boiling Point: 519.1 °C at 760 mmHg
• PKA: pKa 2.29(H2O t = 24.0 I = 0.5 (NaCl)) (Uncertain)
• Flash Point: 267.8 °C
• PSA: 106.35000
• Density: 1.439 g/cm³
• LogP: 2.90300
• Storage Temp.: 0-6°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 202mg/L(20 oC)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 264.06809681
• Heavy Atom Count: 18
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

Sulfamerazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=NC(=NC=C1)NS(=O)(=O)C2=CC=C(C=C2)N
• Uses: Antibacterial.
• Therapeutic Function: Antibacterial

Technology Process of Sulfamerazine

There total 21 articles about Sulfamerazine 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:

4-Methyl-pyrimidin-2-ylamin (108-52-1) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → sulfamerazina (127-79-7)

Guidance literature:

4-Methyl-pyrimidin-2-ylamin; p-acetylaminobenzenesulfonyl chloride; With pyridine; In tetrahydrofuran; at 20 ℃; for 6h;

With sodium hydroxide; for 2h; Reflux;

DOI:10.1016/j.ejmech.2017.04.074

Reference yield:

N-[4-(4-Methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-acetamide (127-73-1) → sulfamerazina (127-79-7)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01262a034 DOI:10.1021/ja01856a046 DOI:10.1021/ja01865a027

Reference yield:

4-Methyl-pyrimidin-2-ylamin (108-52-1) → sulfamerazina (127-79-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: aq. NaOH solution

With pyridine; sodium hydroxide;

DOI:10.1021/ja01262a034 DOI:10.1021/ja01856a046 DOI:10.1021/ja01865a027

upstream raw materials:

2-chloro-4-methylpyrimidine

sulfanilamide

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

4-methyl-2-phenoxy-pyrimidine

Downstream raw materials:

N-[4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-succinamic acid

N-[4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-phthalamic acid

4-formylamino-N-(4-methyl-pyrimidin-2-yl)-benzenesulfonamide

N-cyano-sulfanilic acid-(4-methyl-pyrimidin-2-ylamide)

Refernces

2-Substituted 1,3-Benzoxathiolium Tetrafluoroborates as Efficient Acylating Agents for N,N-Dialkylarylamines

10.1055/s-1986-31696

The research focuses on the utilization of 2-substituted 1,3-benzoxathiolium tetrafluoroborates as efficient acylating agents for N,N-dialkylarylamines in a two-step reaction process. The purpose of this study was to develop a new approach for the acylation of N,N-dialkylarylamines, which typically yields low or moderate ketones when carried out under various conditions with different reagents. The researchers found that the use of these benzoxathiolium derivatives led to high yields (about 90%) of intermediate 2.2-disubstituted 1,3-benzoxathioles, which upon hydrolysis afforded the corresponding ketones in almost quantitative yields. The conclusions drawn from the research highlight the advantages of this new procedure, including mild reaction conditions, selective para-position substitution relative to the dialkylamino group, and the ease of introducing a tertiary acyl group. Key chemicals used in the process include 2-substituted 1,3-benzoxathiolium tetrafluoroborates, N,N-dialkylarylamines, pyridine, acetonitrile, and various substituents such as t-butyl, phenyl, and pentyl groups.