N-Benzylcinnamanilide

Base Information

• Chemical Name: N-Benzylcinnamanilide
• CAS No.: 100978-95-8
• Molecular Formula: C22H19NO
• Molecular Weight: 313.399
• European Community (EC) Number: 662-555-0
• NSC Number: 204182
• Nikkaji Number: J1.560.377A
• Mol file: 100978-95-8.mol

Synonyms:NSC204182;N-BENZYLCINNAMANILIDE;N-Phenyl-N-benzylcinnamamide;SCHEMBL8721921;BDBM435207;AKOS024340084;NSC-204182;US10584134, Example 3-28

Chemical Property of N-Benzylcinnamanilide

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 313.146664230
• Heavy Atom Count: 24
• Complexity: 398

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN(C2=CC=CC=C2)C(=O)C=CC3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)CN(C2=CC=CC=C2)C(=O)/C=C/C3=CC=CC=C3

Technology Process of N-Benzylcinnamanilide

There total 6 articles about N-Benzylcinnamanilide 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: 87.0%

cinnamanilide (3056-73-3,25775-89-7,52393-67-6) + benzyl bromide (100-39-0) → N-benzyl-N-phenylcinnamamide (100978-95-8)

Guidance literature:

cinnamanilide; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 1h;

benzyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃;

DOI:10.1021/ol400743r

Reference yield: 60.0%

carbon dioxide (124-38-9,18923-20-1) + N-benzyl-N-phenylacrylamide + methyl iodide (74-88-4) + phenylboronic acid (98-80-6) → N-benzyl-N-phenylcinnamamide (100978-95-8) + methyl 2-benzyl-3-(benzyl(phenyl)amino)-3-oxopropanoate

Guidance literature:

carbon dioxide; N-benzyl-N-phenylacrylamide; phenylboronic acid; With chloro(1,5-cyclooctadiene)rhodium(I) dimer; N,N,N',N'',N'''-pentamethyldiethylenetriamine; silver trifluoromethanesulfonate; caesium carbonate; In N,N-dimethyl acetamide; at 60 ℃; for 24h; Sealed tube; Green chemistry;

methyl iodide; With potassium carbonate; In N,N-dimethyl acetamide; at 60 ℃; for 2h; regioselective reaction; Green chemistry;

DOI:10.1039/d0gc02667k

Reference yield:

Cinnamic acid (621-82-9) → N-benzyl-N-phenylcinnamamide (100978-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 3 h / 60 °C

2: dichloromethane / 1 h / 20 °C

With thionyl chloride; In dichloromethane;

DOI:10.1021/ol403196h

upstream raw materials:

cinnamanilide

benzyl bromide

Cinnamic acid

N-Benzylaniline

Downstream raw materials:

1-benzyl-3-phenylquinolin-2(1H)-one

3-phenyl-1H-quinolin-2-one

N-benzyl-4-phenyl-1,2,3,4-tetrahydroquinolin-2-one

2,5-diphenyl-1,2,4,5-tetrahydrobenzo[c]azepin-3-one

Refernces

• 1、 Liu, Le,Zhang, Tonghuan,Yang, Yun-Fang,Zhang-Negrerie, Daisy,Zhang, Xinhao,Du, Yunfei,Wu, Yun-Dong,Zhao, Kang. "Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study". . p. 4058 - 4065. Retrieved 2016/06/08.
• 2、 Mai, Wen-Peng,Sun, Gang-Chun,Wang, Ji-Tao,Song, Ge,Mao, Pu,Yang, Liang-Ru,Yuan, Jin-Wei,Xiao, Yong-Mei,Qu, Ling-Bo. "Silver-catalyzed radical tandem cyclization: An approach to direct synthesis of 3-acyl-4-arylquinolin-2(1 H)-ones". . p. 8094 - 8102. Retrieved 2015/03/18.