Isosulfamethoxazole

Base Information

• Chemical Name: Isosulfamethoxazole
• CAS No.: 17103-52-5
• Molecular Formula: C10H11N3O3S
• Molecular Weight: 253.282
• Hs Code.: 2935909550
• UNII: C3XMP53EZ8
• DSSTox Substance ID: DTXSID401300825
• Nikkaji Number: J578.055A
• Wikidata: Q27275156
• ChEMBL ID: CHEMBL283941
• Mol file: 17103-52-5.mol

Synonyms:Isosulfamethoxazole;17103-52-5;Sulfamethoxazole impurity F;4-amino-N-(3-methyl-1,2-oxazol-5-yl)benzenesulfonamide;UNII-C3XMP53EZ8;C3XMP53EZ8;4-Amino-N-(3-methylisoxazol-5-yl)benzenesulfonamide;CHEMBL283941;Sulfanilamide, N1-(3-methyl-5-isoxazolyl)-;5-Sulfanilamido-3-methylisoxazole;Sulfamethoxazole impurity F [USP-MC];Benzenesulfonamide, 4-amino-N-(3-methyl-5-isoxazolyl)-;4-AMINO-N-(3-METHYL-1,2-OXAZOL-5-YL)BENZENE-1-SULFONAMIDE;4-amino-N-(3-methyl-5-isoxazolyl)benzenesulfonamide;DTXSID401300825;BDBM50034474;AKOS000162123;SULFAMETHOXAZOLE IMPURITY F [EP IMPURITY];Q27275156;4-Amino-N-(3-methyl-isoxazol-5-yl)-benzenesulfonamide

Chemical Property of Isosulfamethoxazole

Chemical Property:

• PSA: 106.60000
• LogP: 3.10100
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 253.05211239
• Heavy Atom Count: 17
• Complexity: 346

Purity/Quality:

99% ^*data from raw suppliers

Isosulfamethoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NOC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
• Uses: Isosulfamethoxazole is an impurity of the antibacterial drug Sulfamethoxazole (S699086). It is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

Technology Process of Isosulfamethoxazole

There total 5 articles about Isosulfamethoxazole 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: 76.0%

N-(4-(N-(3-methylisoxazol-5-yl)sulfamoyl)phenyl)acetamide (88614-99-7) → 4-amino-N-(3-methyl-1,2-oxazol-5-yl)benzene-1-sulfonamide (17103-52-5)

Guidance literature:

With sulfuric acid; for 1h;

DOI:10.3987/COM-20-14245

Reference yield:

5-amino-3-methylisoxazole (14678-02-5) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4-amino-N-(3-methyl-1,2-oxazol-5-yl)benzene-1-sulfonamide (17103-52-5)

Guidance literature:

With pyridine; anschliessend Hydrolyse;

DOI:10.1021/ja01264a054

Reference yield:

5-amino-3-methylisoxazole (14678-02-5) + 4-aminobenzenesulfonyl chloride (24939-24-0) → 4-amino-N-(3-methyl-1,2-oxazol-5-yl)benzene-1-sulfonamide (17103-52-5)

Guidance literature:

With pyridine;

DOI:10.1021/jm00029a001

upstream raw materials:

5-amino-3-methylisoxazole

p-acetylaminobenzenesulfonyl chloride

4-aminobenzenesulfonyl chloride

N-(4-(N-(3-methylisoxazol-5-yl)sulfamoyl)phenyl)acetamide

Downstream raw materials:

(E)-N-(4-(N-(3-methylisoxazol-5-yl)sulfamoyl)phenyl)-N'-(7-(trifluoromethyl)quinolin-4-yl)carbamimidothioic acid

N-(3-methylisoxazol-5-yl)-4-(7-(trifluoromethyl)quinolin-4-ylamino)benzenesulfonamide

C₁₉H₁₅ClN₄O₃S

C₂₀H₁₆ClN₅O₃S₂

Refernces

• 1、 Stein, Philip D.,Hunt, John T.,Floyd, David M.,Moreland, Suzanne,Dickinson, Kenneth E. J.,et al.. "The Discovery of Sulfonamide Endothelin Antagonists and the Development of the Orally Active ETA Antagonist 5-(Dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide". . p. 329 - 331. Retrieved 2007/10/02.