Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I)

Base Information

• Chemical Name: Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I)
• CAS No.: 76508-35-5
• Molecular Formula: C12H13NO5S
• Molecular Weight: 283.305
• Mol file: 76508-35-5.mol

Synonyms:Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I);Isopropyl 4-Hydroxy-;Isopropyl 4-Hydroxy- (Piroxicam Impurity I);4-Hydroxy-2H-1,2-benzothiazine-3-carboxylic acid 1-methylethyl ester 1,1-dioxide;NSC 642708

Chemical Property of Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 170℃ (ethanol )
• Boiling Point: 453.09°C at 760 mmHg
• Flash Point: 227.821°C
• PSA: 101.08000
• Density: 1.444g/cm³
• LogP: 2.56630

Purity/Quality:

95% ^*data from raw suppliers

Isopropyl4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate1,1-Dioxide(PiroxicamImpurityI) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Piroxicam impurity I.

Technology Process of Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I)

There total 6 articles about Isopropyl 4-Hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-Dioxide (Piroxicam Impurity I) 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: 85.0%

sodium isopropylate (683-60-3) + (1,1,3-Trioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)-acetic acid isopropyl ester (76508-37-7) → isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (76508-35-5)

Guidance literature:

In isopropyl alcohol; for 0.0833333h; Heating;

Reference yield: 36.0%

methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide (6639-62-9) + sodium isopropylate (683-60-3) → isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (76508-35-5) + methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-14-9)

Guidance literature:

In isopropyl alcohol;

Reference yield:

saccharin sodium salt (128-44-9) → isopropyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (76508-35-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / dimethylformamide / 6 h / 120 °C

2: 85 percent / propan-2-ol / 0.08 h / Heating

In N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide

sodium isopropylate

2-(Isopropoxycarbonylmethyl-sulfamoyl)-benzoic acid isopropyl ester

(1,1,3-Trioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-acetic acid isopropyl ester

Downstream raw materials:

N-methylsaccharin

isopropyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[e][1,2]thiazin-4-one

Refernces

• 1、 Schapira, Celia B.,Perillo, Isabel A.,Lamdan, Samuel. "3-Oxo-1,2-benzoisothiazoline-2-acetic Acid 1,1-Dioxide Derivatives. I. Reaction of Esters with Alkoxides". . p. 1281 - 1288. Retrieved 2007/10/02.