Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate

Base Information

• Chemical Name: Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate
• CAS No.: 111140-90-0
• Molecular Formula: C₁₁H₁₁N₃O₄
• Molecular Weight: 249.226
• DSSTox Substance ID: DTXSID00553203
• Mol file: 111140-90-0.mol

Synonyms:111140-90-0;Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate;SCHEMBL9541279;DTXSID00553203

Chemical Property of Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate

Chemical Property:

• Melting Point: 178-180 °C (decomp)
• PSA: 107.00000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 0.19860
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 249.07495584
• Heavy Atom Count: 18
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC2C(=O)NC(=O)N2

Technology Process of Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate

There total 2 articles about Benzyl (2,5-dioxoimidazolidin-4-yl)carbamate 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:

O-benzyl carbamate (621-84-1) + DL-5-chlorohydantoin (32282-43-2) → 5-<(benzyloxycarbonyl)amino>hydantoin (111140-90-0)

Guidance literature:

In nitromethane; at 50 ℃; for 3h; Yield given;

DOI:10.1021/jm00396a037

Reference yield:

5-hydroxy-hydantoin (29410-13-7) → 5-<(benzyloxycarbonyl)amino>hydantoin (111140-90-0) + 2-Hydroxy-imidazol-4-one

Guidance literature:

With thionyl chloride; O-benzyl carbamate; N,N-dimethyl-formamide; Yield given. Multistep reaction. Yields of byproduct given; 2) CH₃NO₂, 50 deg C;

Reference yield:

bromoacetic acid tert-butyl ester (5292-43-3) + 5-<(benzyloxycarbonyl)amino>hydantoin (111140-90-0) → tert.-butyl <5-(benzyloxycarbonyl)amino-3-hydantoinyl>acetate (159594-34-0) + (5-Benzyloxycarbonylamino-3-tert-butoxycarbonylmethyl-2,4-dioxo-imidazolidin-1-yl)-acetic acid tert-butyl ester

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction. Yields of byproduct given; 1) DMSO, 1 h, 20 deg C, 2) DMSO, RT, overnight;

upstream raw materials:

O-benzyl carbamate

DL-5-chlorohydantoin

5-hydroxy-hydantoin

Downstream raw materials:

tert.-butyl <5-(benzyloxycarbonyl)amino-3-hydantoinyl>acetate