Methyl 4-acetamido-5-chloro-2-ethoxybenzoate

Base Information

• Chemical Name: Methyl 4-acetamido-5-chloro-2-ethoxybenzoate
• CAS No.: 4235-43-2
• Molecular Formula: C12H14ClNO4
• Molecular Weight: 271.7
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID20441173
• Wikidata: Q72486440
• Mol file: 4235-43-2.mol

Synonyms:Methyl 4-acetamido-5-chloro-2-ethoxybenzoate;4235-43-2;Methyl 4-acetylamino-5-chloro-2-ethoxy-benzoate;methyl 4-acetamino-5-chloro-2-ethoxybenzoate;4-ACETAMINO-5-CHLORO-2-ETHOXY METHYL BENZOATE;Methyl4-acetamido-5-chloro-2-ethoxybenzoate;Methyl 4-acetylamino-5-chloro-2-ethoxybenzoate;SCHEMBL7367528;4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester;DTXSID20441173;AMY13507;MFCD06658144;AKOS015890647;AS-11899;CS-0361856;FT-0635186;F83781;A825866;methyl 4-(acetylamino)-5-chloro-2-ethoxybenzoate;J-522286

Chemical Property of Methyl 4-acetamido-5-chloro-2-ethoxybenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• Boiling Point: 448.529 °C at 760 mmHg
• Flash Point: 225.062 °C
• PSA: 64.63000
• Density: 1.276 g/cm³
• LogP: 2.55670
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 271.0611356
• Heavy Atom Count: 18
• Complexity: 311

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl4-Acetamido-5-chloro-2-ethoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC1=CC(=C(C=C1C(=O)OC)Cl)NC(=O)C
• Uses: Methyl 4-acetamido-5-chloro-2-ethoxybenzoate (cas# 4235-43-2) could be a useful therapeutic agent for treating irritable bowel syndrome.

Technology Process of Methyl 4-acetamido-5-chloro-2-ethoxybenzoate

There total 4 articles about Methyl 4-acetamido-5-chloro-2-ethoxybenzoate 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:

methyl 4-acetamido-2-hydroxybenzoate (4093-28-1) → 4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester (4235-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98.4 percent / K₂CO₃ / dimethylformamide / 24 h / 20 - 30 °C

2: NCS / dimethylformamide / 3 h / 70 °C

With N-chloro-succinimide; potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.42

Reference yield:

4-Aminosalicylic acid (65-49-6) → 4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester (4235-43-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sulfuric acid / 2 h / 20 °C

2: acetic acid / 1 h

3: sodium hydroxide / N,N-dimethyl-formamide

4: N-chloro-succinimide / N,N-dimethyl-formamide

With N-chloro-succinimide; sulfuric acid; acetic acid; sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.2174/157018012800389386

Reference yield:

methyl 4-aminosalicylate (4136-97-4) → 4-Acetylamino-5-chloro-2-ethoxy-benzoic acid methyl ester (4235-43-2)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / 1 h

2: sodium hydroxide / N,N-dimethyl-formamide

3: N-chloro-succinimide / N,N-dimethyl-formamide

With N-chloro-succinimide; acetic acid; sodium hydroxide; In N,N-dimethyl-formamide;

DOI:10.2174/157018012800389386

upstream raw materials:

methyl 4-acetamido-2-hydroxybenzoate

4-Aminosalicylic acid

methyl 4-aminosalicylate

Downstream raw materials:

5-Chloro-2-ethoxy-N-[4-(4-fluoro-benzyl)-morpholin-2-ylmethyl]-4-formylamino-benzamide

4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester

4-amino-5-chloro-N-[[4-(2-chlorobenzyl)-2-morpholinyl]methyl]-2-ethoxybenzamide

4-Amino-5-chloro-2-ethoxy-N-[4-(2-fluoro-benzyl)-morpholin-2-ylmethyl]-benzamide

Refernces

• 1、 Kakigami, Takuji,Usui, Toshinao,Tsukamoto, Katsura,Kataoka, Tadashi. "Synthesis and structure-activity relationship of 3-substituted benzamide, benzo[b]furan-7-carboxamide, 2,3-dihydrobenzo[b]furan-7- carboxamide, and indole-5-carboxamide derivatives as selective serotonin 5- HT4 receptor agonists". . p. 42 - 52. Retrieved 2007/10/03.