1-Benzyl-3-cyanoacetylurea

Base Information

• Chemical Name: 1-Benzyl-3-cyanoacetylurea
• CAS No.: 126245-46-3
• Molecular Formula: C11H11N3O2
• Molecular Weight: 217.227
• DSSTox Substance ID: DTXSID90392461
• Nikkaji Number: J1.245.695F
• Wikidata: Q82190721
• Mol file: 126245-46-3.mol

Synonyms:126245-46-3;1-BENZYL-3-CYANOACETYLUREA;1-Benzyl-3-cyanoacetyl Urea;N-(benzylcarbamoyl)-2-cyanoacetamide;Acetamide, 2-cyano-N-[[(phenylmethyl)amino]carbonyl]-;N-(Benzylcarbamoyl)cyanoacetamide;DTXSID90392461;AKOS027446862;1-BENZYL-3-(2-CYANOACETYL)UREA;FT-0662718

Chemical Property of 1-Benzyl-3-cyanoacetylurea

Chemical Property:

• Melting Point: 171-174°C
• PSA: 88.97000
• Density: 1.227g/cm3
• LogP: 1.97078
• Storage Temp.: -20°C Freezer
• Solubility.: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 217.085126602
• Heavy Atom Count: 16
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

1-Benzyl-3-cyanoacetylUrea ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CNC(=O)NC(=O)CC#N
• Uses: Intermediate in the preparation of anticonvulsants

Technology Process of 1-Benzyl-3-cyanoacetylurea

There total 2 articles about 1-Benzyl-3-cyanoacetylurea 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: 89.0%

benzylurea (538-32-9) + cyanoacetic acid (372-09-8) → 1-benzyl-3-(2-cyanoacetyl)urea (126245-46-3)

Guidance literature:

With acetic anhydride; N,N,N',N'-tetramethylguanidinium acetate; at 60 ℃; for 1h; Neat (no solvent);

DOI:10.1039/c1gc15940b

Reference yield:

benzylamine (100-46-9) → 1-benzyl-3-(2-cyanoacetyl)urea (126245-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N,N',N'-tetramethylguanidinium acetate / water / 0.5 h / 60 °C

2: acetic anhydride; N,N,N',N'-tetramethylguanidinium acetate / 1 h / 60 °C / Neat (no solvent)

With acetic anhydride; N,N,N',N'-tetramethylguanidinium acetate; In water;

DOI:10.1039/c1gc15940b

Reference yield: 93.0%

1-benzyl-3-(2-cyanoacetyl)urea (126245-46-3) → 1-benzyl-6-aminouracil (41862-11-7)

Guidance literature:

With 1,1,3,3-tetramethylguanidinium lactate; at 95 ℃; for 1h; Ionic liquid;

DOI:10.1007/s00706-012-0810-9

upstream raw materials:

benzylurea

cyanoacetic acid

benzylamine

Downstream raw materials:

3-Amino-2-oxo-1,4-diaza-spiro[4.5]decane-1,3-dicarboxylic acid 3-amide 1-benzylamide

1-benzyl-6-aminouracil

2-Oxo-1,4-diaza-spiro[4.5]dec-3-ene-1,3-dicarboxylic acid 3-amide 1-benzylamide

Refernces

• 1、 Chavan, Sunil S.,Degani, Mariam S.. "Ionic liquid mediated one-pot synthesis of 6-aminouracils". supporting information; experimental part. p. 296 - 299. Retrieved 2012/03/26.
• 2、 Librowski, Tadeusz,Kubacka, Monika,Meusel, Manuela,Scolari, Silvia,Mueller, Christa E.,Guetschow, Michael. "Evaluation of anticonvulsant and analgesic effects of benzyl- and benzhydryl ureides". . p. 138 - 149. Retrieved 2008/02/08.