N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide Chemical Properties

Melting point:

151-152 °C

Boiling point:

436.4±45.0 °C(Predicted)

Density 

1.42±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

12.08±0.70(Predicted)

color 

White to Off-White

InChI

InChI=1S/C12H9F3N2O2/c1-11(6-19-11)10(18)17-8-3-2-7(5-16)9(4-8)12(13,14)15/h2-4H,6H2,1H3,(H,17,18)

InChIKey

UQUQTWDUTIAAAY-UHFFFAOYSA-N

SMILES

O1CC1(C)C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)=O

CAS DataBase Reference

90357-51-0(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29269090

N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide Usage And Synthesis

Uses

N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methyl-2-oxiranecarboxamide, is an intermediate in synthesis of more complex pharmaceutical compounds. It is used in the synthesis of potential impurities of Bicalutamide (B382000), which is an oral nonsteroidal, anti-androgen drug used for prostate cancer.

Synthesis

General procedure for the synthesis of N-[4-cyano-3-(trifluoromethyl)phenyl]methoxyacrylamide from N-(4-cyano-3-(trifluoromethyl)phenyl)methoxyacrylamide: N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide (50.8 g, 0.2 mol) and phthalic anhydride (47.3 g, 0.32 mol) were dissolved in 350 ml of 1,2-dichloroethane. 50% hydrogen peroxide (23.1 g, 0.34 mol) was added slowly and dropwise at 35?40 °C. The progress of the reaction was monitored by HPLC until the content of the feedstock N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide decreased to less than 0.5% and the reaction was completed. Subsequently, 1,2-dichloroethane was removed by distillation to give the crude product. To the crude product, 300 g of water was added and neutralized by adding 26 g of sodium carbonate. Next, 13 g of sodium sulfate was added and filtered after stirring for 0.5 hours. The filter cake was washed with 50 g of water and dried to give the final product N-[4-cyano-3-(trifluoromethyl)phenyl]-2,3-epoxy-2-methylpropanamide 49 g in 90.7% yield.

References

[1] Journal of Organic Chemistry, 2003, vol. 68, # 26, p. 10181 - 10182
[2] Patent: CN106905265, 2017, A. Location in patent: Paragraph 0015
[3] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 1028 - 1040
[4] Journal of Organometallic Chemistry, 2011, vol. 696, # 5, p. 1049 - 1056
[5] European Journal of Medicinal Chemistry, 2016, vol. 118, p. 230 - 243

N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide(90357-51-0)Related Product Information

• Phenylhydrazine
• Methacrylamide
• N,N'-Methylenebisacrylamide
• 2,2-Dibromo-2-cyanoacetamide
• PHENYL VALERATE
• Acrylamide
• 4-Amino-2-(trifluoromethyl)benzonitrile
• Bicalutamide
• BICALUTAMIDE-D4
• Bicalutamide EP Impurity K
• Desfluoro Bicalutamide
• N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide
• Deshydroxy Bicalutamide
• 3-(4-Fluobenzenesulfhydry)-2-hydroxyl-2-methylpropionic acid
• Bicalutamide EP Impurity F
• N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(2-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
• N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)thio]-2-hydroxy-2-methylpropionamide
• 3-Fluoro-4-desfluoro BicalutaMide