Ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate

Base Information

• Chemical Name: Ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate
• CAS No.: 14181-05-6
• Molecular Formula: C8H11NO4
• Molecular Weight: 185.18
• NSC Number: 132879
• DSSTox Substance ID: DTXSID00931209
• Wikidata: Q82906755
• Mol file: 14181-05-6.mol

Synonyms:14181-05-6;ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate;NSC132879;SCHEMBL18825277;DTXSID00931209;N,N-succinoyl glycine ethyl ester;AKOS008948542;NSC-132879;Ethyl (2,5-dioxopyrrolidin-1-yl)acetate;1-Pyrrolidineaceticacid,2,5-dioxo-,ethyl ester

Chemical Property of Ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate

Chemical Property:

• Vapor Pressure: 3.03E-05mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 355.9 °C at 760 mmHg
• Flash Point: 169 °C
• Density: 1.261 g/cm³
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 185.06880783
• Heavy Atom Count: 13
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN1C(=O)CCC1=O

Technology Process of Ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate

There total 13 articles about Ethyl 2-(2,5-dioxopyrrolidin-1-yl)acetate 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: 98.5%

Succinimide (123-56-8,89963-74-6) + ethyl bromoacetate (105-36-2) → 1-ethoxycarbonylmethyl-pyrrolidine-2,5-dione (14181-05-6)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In toluene; for 20h; Heating;

Reference yield: 82.0%

N-Bromosuccinimide (128-08-5) + ethyl vinyl ether (109-92-2,25104-37-4) → 1-ethoxycarbonylmethyl-pyrrolidine-2,5-dione (14181-05-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 0 - 25 ℃; for 4.5h; regioselective reaction;

DOI:10.1021/acs.orglett.5b03540

Reference yield: 82.0%

→ 1-ethoxycarbonylmethyl-pyrrolidine-2,5-dione (14181-05-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 0 - 25 ℃; for 8h;

upstream raw materials:

succinic acid anhydride

glycine ethyl ester hydrochloride

succinoyl dichloride

GlyOEt*HCl

Downstream raw materials:

1-pyrrolidineethanol

Refernces

• 1、 Prasad, Pragati K.,Reddi, Rambabu N.,Sudalai, Arumugam. "Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters". supporting information. p. 500 - 503. Retrieved 2016/02/18.
• 2、 Gesson, J. P.,Jacquesy, J. C.,Rambaud, D.. "A practial method for N-alkylation of succinimide and glutarimide". . p. 227 - 231. Retrieved 2007/10/02.