Acetylsulfamethoxazole

Base Information

• Chemical Name: Acetylsulfamethoxazole
• CAS No.: 21312-10-7
• Molecular Formula: C12H13N3O4S
• Molecular Weight: 295.319
• Hs Code.: 29350030
• European Community (EC) Number: 244-330-5
• UNII: 3I1988834Q
• DSSTox Substance ID: DTXSID8049044
• Nikkaji Number: J226.185E
• Wikidata: Q27114190
• Metabolomics Workbench ID: 54348
• ChEMBL ID: CHEMBL3560298
• Mol file: 21312-10-7.mol

Synonyms:N(4)-acetylsulfamethoxazole;N(4)-acetylsulphamethoxazole

Chemical Property of Acetylsulfamethoxazole

Chemical Property:

• Appearance/Colour: Brown Solid
• Melting Point: 222 °C
• Refractive Index: 1.622
• PKA: 5.60±0.50(Predicted)
• PSA: 109.68000
• Density: 1.448 g/cm³
• LogP: 2.96900
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 76mg/L(37 oC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 295.06267708
• Heavy Atom Count: 20
• Complexity: 440

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Acetyl Sulfamethoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)NC(=O)C
• Uses: A metabolite of Sulfamethoxazole. A labelled metabolite of Sulfamethoxazole.

Technology Process of Acetylsulfamethoxazole

There total 10 articles about Acetylsulfamethoxazole 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: 80.0%

5-methylisoxazol-3-ylamine (1072-67-9) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N-acetylsulfamethoxazole (21312-10-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ml400259d

Reference yield: 71.9%

sulfamethoxazole (723-46-6) + acetyl chloride (75-36-5) → N-acetylsulfamethoxazole (21312-10-7)

Guidance literature:

With potassium carbonate; In acetone; at 0 - 30 ℃; for 11h;

DOI:10.1007/s11164-011-0327-6

Reference yield:

4-Nitrobenzenesulfonyl chloride (98-74-8) → N-acetylsulfamethoxazole (21312-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 6 h / Ambient temperature

2: H₂ / Pd-C / aq. NaOH / Ambient temperature

3: H₂ / Raney-Ni / aq. NaOH / Ambient temperature

4: pyridine / 0.5 h / 100 °C

With hydrogen; palladium on activated charcoal; nickel; In pyridine; sodium hydroxide;

upstream raw materials:

5-methylisoxazol-3-ylamine

p-acetylaminobenzenesulfonyl chloride

sulfamethoxazole

acetyl chloride

Downstream raw materials:

N-(4-acetylamino-benzenesulfonyl)-N-(5-methyl-isoxazol-3-yl)-acetamide

SMZ chloride

3,4-dichloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)benzamide

4-(3-benzylthioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Refernces

• 1、 Brimacombe, Kyle R.,Walsh, Martin J.,Liu, Li,Vasquez-Valdivieso, Montserrat G.,Morgan, Hugh P.,McNae, Iain,Fothergill-Gilmore, Linda A.,Michels, Paul A. M.,Auld, Douglas S.,Simeonov, Anton,Walkinshaw, Malcolm D.,Shen, Min,Boxer, Matthew B.. "Identification of ML251, a potent inhibitor of T. brucei and T. cruzi phosphofructokinase". . p. 12 - 17. Retrieved 2014.
• 2、 -. "Catalyzed preparation method of sulfamethoxazole". Paragraph 0013; 0016; 0021; 0026; 0031. . Retrieved 2018/02/04.