5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid methyl ester

Base Information

• Chemical Name: 5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid methyl ester
• CAS No.: 247237-38-3
• Molecular Formula: C15H14ClNO4S
• Molecular Weight: 339.799
• Mol file: 247237-38-3.mol

Synonyms:benzoic acid, 5-chloro-2-[[(4-methylphenyl)sulfonyl]amino]-, methyl ester;Methyl 5-chloro-2-{[(4-methylphenyl)sulfonyl]amino}benzoate

Chemical Property of 5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid methyl ester

Chemical Property:

• Vapor Pressure: 1.61E-09mmHg at 25°C
• Melting Point: 115 °C
• Refractive Index: 1.607
• Boiling Point: 483.9 °C at 760 mmHg
• PKA: 7.42±0.10(Predicted)
• Flash Point: 246.5 °C
• PSA: 80.85000
• Density: 1.39 g/cm³
• LogP: 4.38960

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl 5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoate is a reactant used in the synthesis of Tolvaptan (T536650) and its intermediates. Tolvaptan is a nonpeptide arginine vasopressin (AVP) V2 receptor antagonist.

Technology Process of 5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid methyl ester

There total 4 articles about 5-Chloro-2-[[(4-methylphenyl)sulfonyl]amino]benzoic acid methyl ester 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: 95.0%

4-chlorobenzenesulfonyl chloride (5202-89-1) + p-toluenesulfonyl chloride (98-59-9) → N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester (247237-38-3)

Guidance literature:

In pyridine; at 20 ℃; for 18h;

Reference yield:

5-chloro-2-nitrobenzoic acid (2516-95-2) → N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester (247237-38-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / K₂CO₃ / acetone / 0.5 h / Heating

2: SnCl₂*2H₂O; conc. HCl / ethanol / 20 °C

3: 85 percent / pyridine / 20 °C

With pyridine; hydrogenchloride; potassium carbonate; tin(ll) chloride; In ethanol; acetone; 1: Esterification / 2: Reduction / 3: Tosylation;

DOI:10.1016/S0968-0896(99)00101-7

Reference yield:

methyl 5-chloro-2-nitrobenzoate (51282-49-6) → N-p-toluenesulfonyl-5-chloro-anthranilic acid methyl ester (247237-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: SnCl₂*2H₂O; conc. HCl / ethanol / 20 °C

2: 85 percent / pyridine / 20 °C

With pyridine; hydrogenchloride; tin(ll) chloride; In ethanol; 1: Reduction / 2: Tosylation;

DOI:10.1016/S0968-0896(99)00101-7

upstream raw materials:

4-chlorobenzenesulfonyl chloride

p-toluenesulfonyl chloride

5-chloroanthranilic acid

5-chloro-2-nitrobenzoic acid

Downstream raw materials:

4'-chloro-N-isopropyl-2'-methoxycarbonyl-p-toluenesulfonanilide

4'-chloro-2'-methoxycarbonyl-N-methyl-p-toluenesulfonanilide

5-(N-allylamino)-7-chloro-1-[4-[(2-methylbenzoyl)amino]benzoyl]-2,3,4,5-tetrahydro-1H-1-benzazepine

7-chloro-1-[3-chloro-4-[(2-methylbenzoyl)amino]benzoyl]-5-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine

Refernces

• 1、 -. "PROCESS FOR PREPARING TOLVAPTAN INTERMEDIATES". Paragraph 0050; 0051. . Retrieved 2013/07/31.
• 2、 Theeraladanon, Chumpol,Arisawa, Mitsuhiro,Nishida, Atsushi,Nakagawa, Masako. "A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): Its application to the synthesis of key intermediates for anti-malarial agents". . p. 3017 - 3035. Retrieved 2007/10/03.