| Identification | More | [Name]
N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide epoxide | [CAS]
90357-51-0 | [Synonyms]
n-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyloxirane-2-carboxamide
N-4-CYANO-3-(TRIFLUOROMETHYL)PHENYLMETHACRYLAMIDE EPOXIDE
1,2-EPOXY-2-METHYL-N-[4-CYANO-3-(TRIFLUOROMETHYL)]
1,2-Epoxy-2-methyl-N[4-cyano-3(trifluoromethyl)-phenyl] propanamide (Intermediate for Bicalutamide)
1,2-Epoxy-2-Methyl-N[4-Cyano-3(Trifluoromethyl)-Phenyl]Propanamide
N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-METHYL-2-OXIRANE CARBOXAMIDE
N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl-Oxiranecarboxamide
N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methyl-oxiranecarboxamine
1,2-Epoxy-2-methyl-N-(4-cyano-3-trifluoromethyl)-phenyl)propaneamide
N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]METHACRYLAMIDE EPOXIDE (INTERMEDIATE OF BICALUTAMIDE)
4’-Cyano-3’-trifluoromethyl-2,3-epoxy-2-methylpropioanilide | [EINECS(EC#)]
618-536-4 | [Molecular Formula]
C12H9F3N2O | [MDL Number]
MFCD08460201 | [Molecular Weight]
254.21 | [MOL File]
90357-51-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
151-152 °C | [Boiling point ]
436.4±45.0 °C(Predicted) | [density ]
1.42±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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) |
| Hazard Information | Back Directory | [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 |
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