N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide

Base Information

• Chemical Name: N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide
• CAS No.: 90356-78-8
• Molecular Formula: C18H14F4N2O2S
• Molecular Weight: 398.381
• Hs Code.: 29242990
• European Community (EC) Number: 618-533-8
• UNII: 135IE10O4Y
• DSSTox Substance ID: DTXSID301020577
• Nikkaji Number: J2.054.394I
• Wikidata: Q27251480
• ChEMBL ID: CHEMBL171543
• Mol file: 90356-78-8.mol

Synonyms:90356-78-8;N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide;Bicalutamide Sulfide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide;Bicalutamide sulfide, (+/-)-;Bicalutamide impurity J [EP];UNII-135IE10O4Y;135IE10O4Y;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylthio)-2-hydroxy-2-methylpropanamide;EC 618-533-8;N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluoro-phenyl)thio)-2-hydroxy-2-methylpropanamide;N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-(4-fluorophenylsulfanyl)-2-hydroxy-2-methylpropionamide;N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methylpropanamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropanamide;(2RS)-N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfanyl)-2-hydroxy-2-methylpropanamide;Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methyl-;Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methyl-, (+/-)-;Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methyl-;C18H14F4N2O2S;(2RS)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenylsulfanyl)-2-hydroxy-2-methylpropionamide;Bicalutamide Imp. J (EP);Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methyl-, (+/-)-;Bicalutamide Impurity J;SCHEMBL899788;CHEMBL171543;DTXSID301020577;MFCD08235143;AKOS015836118;CS-O-07363;AC-17498;DS-17521;Propanamide,N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methyl-;AM20041369;BICALUTAMIDE IMPURITY J [EP IMPURITY];CS-0154972;FT-0642164;Q27251480;4'-Cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide;4'-cyano-3-(4-fluorophenylthio)2-hydroxy-2-methyl-3'-trifluoromethylpropionanilide;N-[3-(Trifluoromethyl)-4-cyanophenyl]-2-hydroxy-2-[(4-fluorophenylthio)methyl]propionamide;3-(4-fluorophenylthio)-N-(4-Cyano-3-(trifluoromethyl) phenyl)-2-hydroxy-2-methylpropanamide;N-(4'-Cyano-3'-trifluoro methylphenyl)-3-(4''-fluor rophenilthio)-2-hydroxy-2-methylpropionamide;N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-fluorophenylthio)-2-hydroxy-2-methylpropanamide;N-[4-cyano-3-(trifluoromethyl)-phenyl-]-3-[4-fluorophenylthio]-2-hydroxy-2-methyl-propionamide;N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide;N-[4-cyano-3-trifluoromethyl-phenyl]-3-[4-fluorophenyl-thio]-2-hydroxy-2-methyl-propionamide

Chemical Property of N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 109-111°C
• Refractive Index: 1.585
• Boiling Point: 565.588 °C at 760 mmHg
• PKA: 12.31±0.29(Predicted)
• Flash Point: 295.857 °C
• PSA: 98.42000
• Density: 1.43 g/cm³
• LogP: 4.27098
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 398.07121152
• Heavy Atom Count: 27
• Complexity: 571

Purity/Quality:

99% ^*data from raw suppliers

BicalutamideSulfide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSC1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
• Uses: Bicalutamide intermediate.

Technology Process of N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide

There total 17 articles about N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide 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: 98.0%

4-Fluorothiophenol (371-42-6) + N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide (90357-51-0) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide (90356-78-8)

Guidance literature:

4-Fluorothiophenol; N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide; With methanol; sodium hydroxide; water; at 0 - 25 ℃; for 3.5h;

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide; With hydrogenchloride; water; at 5 ℃; for 3h; pH=< 7;

Reference yield: 79.0%

4-Fluorothiophenol (371-42-6) + N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide (90357-53-2) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide (90356-78-8)

Guidance literature:

4-Fluorothiophenol; N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide; In 1,2-dichloro-ethane; acetonitrile; at 20 ℃; for 4h;

With triphenylphosphine; In 1,2-dichloro-ethane; acetonitrile; for 2h;

DOI:10.1039/c6cc01937d

Reference yield: 54.0%

N-(4-cyano-3-iodophenyl)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methylpropanamide + 2-bromoethanol (540-51-2) → N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfanyl]-2-hydroxy-2-methylpropanamide (90356-78-8)

Guidance literature:

N-(4-cyano-3-iodophenyl)-2-hydroxy-3-(4-hydroxyphenoxy)-2-methylpropanamide; With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; acetone; at 20 ℃; for 0.5h;

2-bromoethanol; In N,N-dimethyl-formamide; acetone; Reflux;

DOI:10.3390/molecules26092525

upstream raw materials:

4-Fluorothiophenol

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide

N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide

4-fluoro-2-(trifluoromethyl)benzonitrile

Downstream raw materials:

N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfinyl-2-hydroxy-2-methyl-propanamide

Bicalutamide

4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-2-(4-fluoro-phenylsulfanyl)-1-methyl-ethyl ester

Refernces

• 1、 Kim, Ga Yeong,Song, Chae Won,Yang, Yo-Sep,Lee, Na-Rae,Yoo, Hyung-Seok,Son, Seung Hwan,Lee, Soo Jin,Park, Jong Seon,Lee, Jong Kil,Inn, Kyung-Soo,Kim, Nam-Jung. "Chemical degradation of androgen receptor (Ar) using bicalutamide analog–thalidomide protacs". . . Retrieved 2021/05/26.
• 2、 Bassetto, Marcella,Ferla, Salvatore,Pertusati, Fabrizio,Kandil, Sahar,Westwell, Andrew D.,Brancale, Andrea,McGuigan, Christopher. "Design and synthesis of novel bicalutamide and enzalutamide derivatives as antiproliferative agents for the treatment of prostate cancer". supporting information. p. 230 - 243. Retrieved 2016/05/10.