Tetraethyl ranelate

Base Information

• Chemical Name: Tetraethyl ranelate
• CAS No.: 58194-26-6
• Molecular Formula: C20H26N2O8S
• Molecular Weight: 454.501
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30482577
• Wikidata: Q72505039
• Mol file: 58194-26-6.mol

Synonyms:Tetraethyl ranelate;58194-26-6;Diethyl 2,2'-((3-cyano-4-(2-ethoxy-2-oxoethyl)-5-(ethoxycarbonyl)thiophen-2-yl)azanediyl)diacetate;ethyl 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate;C20H26N2O8S;5-[Bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid ethyl ester;ranelic acid tetraethyl ester;SCHEMBL2552584;DTXSID30482577;BCP26338;MFCD09839706;AKOS015896097;AC-5929;AS-11402;P-AMINOPHENYLALPHA-D-MANNOPYRANOSIDE;CS-0139557;FT-0656917;H11002;A831780;5-[bis(ethoxycarbonylmethyl)amino]-4-cyano-2-ethoxycarbonyl- 3-thiophenepropionate;5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-3-(2-ethoxy-2-oxoethyl)-2-thiophenecarboxylic acid ethyl ester;Diethyl2,2'-((3-cyano-4-(2-ethoxy-2-oxoethyl)-5-(ethoxycarbonyl)thiophen-2-yl)azanediyl)diacetate;ethyl 5-[bis(2-ethoxy-2-oxidanylidene-ethyl)amino]-4-cyano-3-(2-ethoxy-2-oxidanylidene-ethyl)thiophene-2-carboxylate

Chemical Property of Tetraethyl ranelate

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 2.06E-13mmHg at 25°C
• Melting Point: 103-106 °C
• Refractive Index: 1.538
• Boiling Point: 579.2 °C at 760 mmHg
• PKA: -3.75±0.50(Predicted)
• Flash Point: 304.1 °C
• PSA: 160.47000
• Density: 1.28 g/cm³
• LogP: 1.83468
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 16
• Exact Mass: 454.14098697
• Heavy Atom Count: 31
• Complexity: 672

Purity/Quality:

99% ^*data from raw suppliers

TetraethylRanelate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1=C(SC(=C1C#N)N(CC(=O)OCC)CC(=O)OCC)C(=O)OCC

Technology Process of Tetraethyl ranelate

There total 4 articles about Tetraethyl ranelate 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: 91.0%

ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl) thiophene-2-carboxylate (58168-20-0) + ethyl bromoacetate (105-36-2) → 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid ethyl ester (58194-26-6)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; Reflux; Autoclave; Large scale;

Reference yield: 91.0%

ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl) thiophene-2-carboxylate (58168-20-0) + chloroacetic acid ethyl ester (105-39-5) → 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid ethyl ester (58194-26-6)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In water; acetone; for 3h; Reagent/catalyst; Concentration; Time; Reflux;

Reference yield:

diethyl 1,3-acetonedicarboxylate (105-50-0) → 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid ethyl ester (58194-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / morpholine; sulfur / ethanol / 2 h / Heating

2: 89 percent / potassium carbonate; Adogen 464 / acetone / 5 h / Heating

With morpholine; adogen 464; potassium carbonate; sulfur; In ethanol; acetone; 1: Gewald reaction;

DOI:10.1002/hc.20290

upstream raw materials:

ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl) thiophene-2-carboxylate

ethyl bromoacetate

diethyl 1,3-acetonedicarboxylate

chloroacetic acid ethyl ester

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF STRONTIUM RANELATE, INTERMEDIATE OR HYDRATES THEREOF". . . Retrieved 2013/08/15.
• 2、 Hongtao, Wei,Jin, Cai,Min, Sun,Min, Ji. "Synthesis of substituted thieno[2,3-b]pyrroles". . p. 236 - 238. Retrieved 2008/02/07.