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ChemicalBook--->CAS DataBase List--->330792-69-3

330792-69-3

330792-69-3 Structure

330792-69-3 Structure
IdentificationBack Directory
[Name]

Propanedinitrile, 2-[Methoxy(4-phenoxyphenyl)Methylene]-
[CAS]

330792-69-3
[Synonyms]

Zanubrutinib Impurity 5
Zanubrutinib Related Compound 3
1,1-Dicyano-2-methoxy-2-(4-phenoxyphenyl)ethene
2-(Methoxy(4- phenoxyphenyl)Methylene)Malononitri
2-(Methoxy(4-phenoxyphenyl)Methylene)Malononitrile
2-[Methoxy(4-phenoxyphenyl)methylene]propanedinitrile
2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile
ROPANEDINITRILE, 2-[METHOXY(4-PHENOXYPHENYL)METHYLENE]-
Propanedinitrile, 2-[Methoxy(4-phenoxyphenyl)Methylene]-
Intermediate of Ibrutinib, Note separate 2-[(4-phenoxy-phenyl)-methoxy-methylene]-malononitrile
[Molecular Formula]

C17H12N2O2
[MDL Number]

MFCD20140315
[MOL File]

330792-69-3.mol
[Molecular Weight]

276.29
Chemical PropertiesBack Directory
[Boiling point ]

471.1±45.0 °C(Predicted)
[density ]

1.199±0.06 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,2-8°C
[Appearance]

Light yellow to yellow Solid
[InChI]

InChI=1S/C17H12N2O2/c1-20-17(14(11-18)12-19)13-7-9-16(10-8-13)21-15-5-3-2-4-6-15/h2-10H,1H3
[InChIKey]

IRVRZQLHMPWLLY-UHFFFAOYSA-N
[SMILES]

C(#N)/C(=C(/OC)\C1=CC=C(OC2=CC=CC=C2)C=C1)/C#N
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P280-P305+P351+P338
Spectrum DetailBack Directory
[Spectrum Detail]

Propanedinitrile, 2-[Methoxy(4-phenoxyphenyl)Methylene]-(330792-69-3)1HNMR
Hazard InformationBack Directory
[Synthesis]

4-PHENOXYBENZOYL CHLORIDE

1623-95-6

Dimethyl sulfate

77-78-1

Malononitrile

109-77-3

Propanedinitrile, 2-[Methoxy(4-phenoxyphenyl)Methylene]-

330792-69-3

6.6 g of malononitrile (0.1 mol), 4.8 g of sodium hydride (0.2 mol, 80% dispersed in paraffin) and 100 mL of freshly treated anhydrous tetrahydrofuran were added to a three-neck flask. Under stirring conditions, 50 mL of tetrahydrofuran solution containing 4-phenoxybenzoyl chloride (23.2 g, 0.1 mol) was slowly added dropwise to the reaction system. After 2 hours of reaction at room temperature, 250 mL of 1 M dilute hydrochloric acid was added and stirring was continued for 30 minutes, followed by three extractions with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated to give a solid. The solid was dissolved in a mixture of 150 mL of dioxane and 50 mL of saturated sodium bicarbonate solution, followed by the addition of dimethyl sulfate (37.8 g, 0.3 mol), and the reaction mixture was heated to 80 °C. The reaction was stirred at 90 °C for 3 h. The completion of the reaction was monitored by TLC. At the end of the reaction, 400 mL of deionized water was added and extracted three times with methyl tert-butyl ether. The organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the resulting crude product was recrystallized from methanol to give 17.6 g of white solid 2-(methoxy(4-phenoxyphenyl)methylene)malononitrile in 63.8% yield.

[References]

[1] Patent: US2016/264584, 2016, A1. Location in patent: Paragraph 0019
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