2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-(phenylmethyl)-, methyl ester, 1,1-dioxide

Base Information

• Chemical Name: 2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-(phenylmethyl)-, methyl ester, 1,1-dioxide
• CAS No.: 35511-21-8
• Molecular Formula: C17H15NO5S
• Molecular Weight: 345.376
• Mol file: 35511-21-8.mol

Synonyms:

Chemical Property of 2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-(phenylmethyl)-, methyl ester, 1,1-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-(phenylmethyl)-, methyl ester, 1,1-dioxide

There total 8 articles about 2H-1,2-Benzothiazine-3-carboxylic acid, 4-hydroxy-2-(phenylmethyl)-, methyl ester, 1,1-dioxide 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: 87.6%

benzyl chloride (100-44-7) + methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-14-9) → methyl 2-benzyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (35511-21-8)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 4h;

DOI:10.1016/j.ejmech.2017.10.036

Reference yield:

saccharin (81-07-2) → methyl 2-benzyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (35511-21-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, 4 h

2: 25percent MeONa/MeOH / toluene / 4 h / 80 °C

3: 1M aq. NaOH / ethanol / 24 h / Ambient temperature

With methanol; sodium hydroxide; sodium methylate; sodium hydride; In ethanol; toluene;

DOI:10.1021/jm9607010

Reference yield:

methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-14-9) + iodomethylbenzene (620-05-3) → methyl 2-benzyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (35511-21-8)

Guidance literature:

With sodium hydroxide; In ethanol; for 24h; Ambient temperature;

DOI:10.1021/jm9607010

upstream raw materials:

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

iodomethylbenzene

saccharin

saccharin sodium salt

Refernces

• 1、 Saddique, Furqan Ahmad,Zaib, Sumera,Jalil, Saquib,Aslam, Sana,Ahmad, Matloob,Sultan, Sadia,Naz, Humera,Iqbal, Mazhar,Iqbal, Jamshed. "Synthesis, monoamine oxidase inhibition activity and molecular docking studies of novel 4-hydroxy-N′-[benzylidene or 1-phenylethylidene]-2-H/methyl/benzyl-1,2-benzothiazine-3-carbohydrazide 1,1-dioxides". . p. 1373 - 1386. Retrieved 2017/11/13.
• 2、 Berryman,Edmunds,Bunker,Haleen,Bryant,Welch,Doherty. "Endothelin receptor antagonists: Synthesis and structure-activity relationships of substituted benzothiazine-1,1-dioxides". . p. 1447 - 1456. Retrieved 2007/10/03.