1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate

Base Information

• Chemical Name: 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate
• CAS No.: 1233485-20-5
• Molecular Formula: C₄H₆O₄*C₁₈H₂₀F₂N₄O₂S
• Molecular Weight: 512.534
• Mol file: 1233485-20-5.mol

Synonyms:

Chemical Property of 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate

There total 10 articles about 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate 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: 90.0%

succinic acid (110-15-6) + 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide (1033221-94-1) → 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate (1233485-20-5)

Guidance literature:

In ethanol; water; at 22 - 28 ℃; Large scale reaction;

DOI:10.1021/op100113j

Reference yield:

2,6-difluoro-N-(2-nitrophenyl)aniline (1033225-43-2) → 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate (1233485-20-5)

Guidance literature:

Multi-step reaction with 8 steps

1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 2 h / 45 °C / 3087.28 - 3604.44 Torr / Large scale reaction

2: tetrahydrofuran / 11.21 h / 20 - 30 °C / Large scale reaction

3: thionyl chloride; triethylamine / toluene / 3.58 h / -6 - 10 °C / Large scale reaction

4: sodium hypochlorite; tetrabutylammonium sulfate / dichloromethane; water / 1.37 h / 10 - 30 °C / Large scale reaction

5: water; sodium hydroxide / methanol / 1.5 h / 20 - 30 °C / Large scale reaction

6: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.68 h / -5 - 26 °C / Large scale reaction

7: hydrogenchloride; water / tetrahydrofuran / 0.75 h / 52 - 58 °C / Large scale reaction

8: ethanol; water / 22 - 28 °C / Large scale reaction

With hydrogenchloride; sodium hypochlorite; thionyl chloride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; water; hydrogen; tetrabutylammonium sulfate; triethylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; 6: Mitsunobu reaction;

DOI:10.1021/op100113j

Reference yield:

1-(2,6-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (1033225-45-4) → 1-(2,6-difluorophenyl)-1,3-dihydro-3-[2-(1-piperazinyl)ethyl]benzothiadiazole-S,S-dioxide succinate (1233485-20-5)

Guidance literature:

Multi-step reaction with 3 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.68 h / -5 - 26 °C / Large scale reaction

2: hydrogenchloride; water / tetrahydrofuran / 0.75 h / 52 - 58 °C / Large scale reaction

3: ethanol; water / 22 - 28 °C / Large scale reaction

With hydrogenchloride; di-isopropyl azodicarboxylate; water; triphenylphosphine; In tetrahydrofuran; ethanol; water; 1: Mitsunobu reaction;

DOI:10.1021/op100113j

upstream raw materials:

2,6-difluoro-N-(2-nitrophenyl)aniline

N-(2,6-difluorophenyl)benzene-1,2-diamine

1-(2,6-difluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

1-(tert-butyloxycarbonyl)-3-(2,6-difluorophenyl)-1,3-dihydrobenzothiadiazole-S,S-dioxide

Refernces