5-Benzylidene-3-phenylrhodanine

Base Information

• Chemical Name: 5-Benzylidene-3-phenylrhodanine
• CAS No.: 13037-56-4
• Molecular Formula: C16H11 N O S2
• Molecular Weight: 297.401
• Wikidata: Q76145772
• Mol file: 13037-56-4.mol

Synonyms:5-Benzylidene-3-phenylrhodanine;BRN 0218849;Rhodanine, 5-benzylidene-3-phenyl-;13037-56-4;(5E)-5-benzylidene-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one;5-Benzylidene-3-phenyl-2-thioxo-thiazolidin-4-one;C16H11NOS2;SCHEMBL10035996;Rhodanine, 5-benzylidene-3-phenyl;C16-H11-N-O-S2;AKOS000321944;LS-143535;Z44354602

Chemical Property of 5-Benzylidene-3-phenylrhodanine

Chemical Property:

• Vapor Pressure: 4E-08mmHg at 25°C
• Boiling Point: 445.3°C at 760 mmHg
• Flash Point: 223.1°C
• Density: 1.39g/cm³
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 297.02820632
• Heavy Atom Count: 20
• Complexity: 420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C2C(=O)N(C(=S)S2)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)/C=C/2\C(=O)N(C(=S)S2)C3=CC=CC=C3

Technology Process of 5-Benzylidene-3-phenylrhodanine

There total 5 articles about 5-Benzylidene-3-phenylrhodanine 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: 90.0%

3-phenylrhodanine (1457-46-1) + benzaldehyde (100-52-7) → 5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one (13037-56-4)

Guidance literature:

With piperidine; acetic acid; In toluene; Reflux;

DOI:10.1039/c4ob02625j

Reference yield: 72.0%

3-phenylrhodanine (1457-46-1) + 5-benzylidene-2-morpholino-1,3-thiazol-4(5H)-one (36937-44-7) → 5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one (13037-56-4)

Guidance literature:

3-phenylrhodanine; With sodium; In toluene; for 1h; Heating;

5-benzylidene-2-morpholino-1,3-thiazol-4(5H)-one; In toluene; for 4h; Heating;

DOI:10.1007/s007060200092

Reference yield:

phenyl isothiocyanate (103-72-0) → 5-benzylidene-3-phenyl-2-thioxothiazolidin-4-one (13037-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: NaOAc; HOAc

With sodium acetate; acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/j.bmcl.2005.05.034

upstream raw materials:

benzaldehyde

3-phenylrhodanine

5-benzylidene-2-morpholino-1,3-thiazol-4(5H)-one

phenyl isothiocyanate

Downstream raw materials:

5-Benzyliden-3-phenyl-4-oxothiazolidin-2-thion-S-oxid

(4-Fluoro-phenyl)-dithiocarbamic acid (4-oxo-3-phenyl-2-thioxo-thiazolidin-5-yl)-phenyl-methyl ester

5-Benzyliden-3-phenylthiazolidin-2,4-dion

Refernces

• 1、 Kandeel, Kamal A.,Youssef, Ali M.,EI-Bestawy, Hany M.,Omar, Mohamed T.. "Reactions of N,N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5H)-ones with CH acids". . p. 1211 - 1219. Retrieved 2002.
• 2、 Yadav,Dubey, Suman,Singh, Smita. "A convenient synthesis of 3,5-diarylthieto[2,3-d]thiazole-2-thiones, and expansion of their thiete ring with carbon disulphide". . p. 1234 - 1237. Retrieved 2007/10/03.