118854-48-1

Basic information

• Product Name: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide
• Synonyms: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide;Isopropyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide;4-HYDROXY-2-METHYL-1H-1,2-BENZOTHIAZINE-3-CARBOXYLICACIDISOPROPYLESTER-1,1-DIOXIDE;4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropylester-1,1-dioxide (intermediate of piroxicam);Isopropyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylater 1,1-dioxide;Isopropyl 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity L);Isopropyl 4-Hydroxy-2-methyl-;Meloxicam Related Compound C (30 mg) (Isopropyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide)
• CAS NO: 118854-48-1
• Molecular Formula: C₁₃H₁₅NO₅S
• Molecular Weight: 297.3269
• Product Categories: Organic acids;(intermediate of piroxicam);Aromatics;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 118854-48-1.mol

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 450.485 °C at 760 mmHg
• Flash Point: 226.246 °C
• Appearance: /
• Density: 1.408
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide(118854-48-1)
• EPA Substance Registry System: 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide(118854-48-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 118854-48-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide is used as a reference impurity in the quality control and analysis of Piroxicam and Meloxicam. Its presence in these drugs is monitored and controlled to ensure the safety, efficacy, and purity of the final pharmaceutical products.
In the pharmaceutical industry, maintaining the quality and purity of drugs is crucial for their safety and effectiveness. Impurities such as 4-Hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid isopropyl ester 1,1-dioxide can be used as reference materials to develop and validate analytical methods for detecting and quantifying impurities in drug substances. This helps in ensuring that the final products meet the required standards and regulations, ultimately protecting the health and well-being of patients.

Upstream product

• 127861-96-5 2-(Isopropoxycarbonylmethyl-methyl-sulfamoyl)-benzoic acid isopropyl ester 
• 113412-07-0 methyl 2-(N-methyl-N-(methoxycarbonylmethyl)sulfamoyl)benzoate 
• 67-63-0 isopropyl alcohol 
• 76508-35-5 isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide 
• 74-88-4 methyl iodide 
• 76508-37-7 (1,1,3-Trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid isopropyl ester 

Downstream Products

• 15448-99-4 N-methylsaccharin 
• 36322-90-4 Piroxicam 

Relevant articles and documents

Ring contraction of 3-carboxamide or 3-carboxylate of 4-hydroxy-2- methyl-2H-1,2-benzothiazine-1,1-dioxide and analogous 1 (2H)-isoquinolinone- 3-carboxylate

A novel ring transformation of 3-carboxylate or 3-carboxamide of 4- hydroxy-2-methyl-2H-1,2-benzothiazine-1,1-dioxide and analogous 1(2H)- isoquinolinone-3-carboxylate to the 5-membered rings upon the reaction with carbonyl compounds in the presence of primary or secondary amines is described.

TITANIUM-MEDIATED DIECKMANN CONDENSATION

The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)-benzoates Ia and Ib with titanium tetrachloride-tert-amine or butyltitanium ate complex III affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IIa and IIb which are the piroxicam intermediates.

CONDITIONS OF THE DIECKMANN CONDENSATION OF ALKYL 2-(N-METHYL-N-(ALKOXYCARBONYLMETHYL)SULFAMOYL-BENZOATES

The Dieckmann condensation of alkyl 2-(N-methyl-N-(alkoxycarbonylmethyl)sulfamoyl)benzoates IIIa-IIIe with various bases affords alkyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxides IVa-IVe which are intermediates in the synthesis of antiinflammatory drug piroxicam.The yields of benzothiazines IVa-IVe depend mostly on the nature of a base, reaction temperature and solvent used for these condensations.Hitherto undescribed esters IIIb-IIIe were sythesized and their structures were confirmed by 1H and 13C NMR, and mass spectra.

Process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

A process for obtaining 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, which may be used as a non-steroidal analgesic and anti-inflammatory drug. The process comprises reacting saccharin sodium with isopropyl chloroacetate in dimethylformamide, reacting the resultant isopropyl 3-oxo-1,2-benzoisothiazoline-2-acetate 1,1-dioxide with sodium isopropylate in isopropanol to produce an intermediate which, when methylated in an aqueous-alcoholic basic medium with dimethyl sulfate, gives an intermediate compound which when condensed with 2-aminopyridine in xylene, yields 4-hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazone-3-carboxamide 1,1-dioxide.