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Crystal and mol ­ ecular structure of (2 Z ,5 Z )-3-(2-meth ­ oxy ­ phen ­ yl)-2-[(2-meth ­ oxy ­ phen ­ yl)imino]-5-(4-nitro ­ benzyl ­ idene)thia ­ zolidin-4-one

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ABSTRACT

In the title compound, C24H19N3O5S, the thia­zole ring (r.m.s. deviation = 0.012 Å) displays a planar geometry and is surrounded by three fragments, two meth­oxy­phenyl and one nitro­phenyl. The thia­zole ring is almost in the same plane as the nitro­phenyl ring, making a dihedral angle of 20.92 (6)°. The two meth­oxy­phenyl groups are perpendicular to the thia­zole ring [dihedral angles of 79.29 (6) and 71.31 (7)° and make a dihedral angle of 68.59 (7)°. The mol­ecule exists in an Z,Z conformation with respect to the C=N imine bond. In the crystal, a series of C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds, augmented by several π–π(ring) inter­actions, produce a three-dimensional architecture of mol­ecules stacked along the b-axis direction. The experimentally derived structure is compered with that calculated theoretically using DFT(B3YLP) methods.

No MeSH data available.


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Chemical pathways showing the formation of the title compound. Reagents and conditions: (a) CS2, EtOH, 346 K; (b) BrAcOEt, EtOH, CH3COONa 348 K; (c) NO2C6H4CHO; CH3COOH; CH3COONa, 365 K.
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fig4: Chemical pathways showing the formation of the title compound. Reagents and conditions: (a) CS2, EtOH, 346 K; (b) BrAcOEt, EtOH, CH3COONa 348 K; (c) NO2C6H4CHO; CH3COOH; CH3COONa, 365 K.

Mentions: The synthesis of the title compound was performed according to the scheme in Fig. 4 ▸. To a solution of o-anisidine (0.02 mol) in ethanol (10 mL) was added carbon di­sulfide (0.01 mol) and the resulting solution was refluxed for 6 h to gave N,N′ diaryl thio­uria. (0.01 mol) of the compound and (0.01 mol) of ethyl bromo­acetate were refluxed in 40 mL of absolute ethanol in the presence of (0.04 mol) of anhydrous CH3COONa for 2 h. The precipitate thus obtained was filtered, dried and recrystallized from ethanol to formed 3-N-(2-meth­oxy­phen­yl)-2-N′-(2-meth­oxy­phenyl­imino)-thia­zolidin-4-one. 4-Nitro­benz­alde­hyde (0.01 mol) was added to a solution of the latter compound in 10 mL of acetic acid containing three equivalents of anhydrous sodium acetate. The reaction mixture was refluxed for 4 h and monitored by TLC on silica gel using di­chloro­methane:ethyl acetate (9:1) as a solvent system. The separated solid was filtered, washed with cold water and dried to give the title compound. Single crystals suitable for X-ray diffraction were obtained from ethanol solution.


Crystal and mol ­ ecular structure of (2 Z ,5 Z )-3-(2-meth ­ oxy ­ phen ­ yl)-2-[(2-meth ­ oxy ­ phen ­ yl)imino]-5-(4-nitro ­ benzyl ­ idene)thia ­ zolidin-4-one
Chemical pathways showing the formation of the title compound. Reagents and conditions: (a) CS2, EtOH, 346 K; (b) BrAcOEt, EtOH, CH3COONa 348 K; (c) NO2C6H4CHO; CH3COOH; CH3COONa, 365 K.
© Copyright Policy - open-access
Related In: Results  -  Collection

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Show All Figures
getmorefigures.php?uid=PMC5382610&req=5

fig4: Chemical pathways showing the formation of the title compound. Reagents and conditions: (a) CS2, EtOH, 346 K; (b) BrAcOEt, EtOH, CH3COONa 348 K; (c) NO2C6H4CHO; CH3COOH; CH3COONa, 365 K.
Mentions: The synthesis of the title compound was performed according to the scheme in Fig. 4 ▸. To a solution of o-anisidine (0.02 mol) in ethanol (10 mL) was added carbon di­sulfide (0.01 mol) and the resulting solution was refluxed for 6 h to gave N,N′ diaryl thio­uria. (0.01 mol) of the compound and (0.01 mol) of ethyl bromo­acetate were refluxed in 40 mL of absolute ethanol in the presence of (0.04 mol) of anhydrous CH3COONa for 2 h. The precipitate thus obtained was filtered, dried and recrystallized from ethanol to formed 3-N-(2-meth­oxy­phen­yl)-2-N′-(2-meth­oxy­phenyl­imino)-thia­zolidin-4-one. 4-Nitro­benz­alde­hyde (0.01 mol) was added to a solution of the latter compound in 10 mL of acetic acid containing three equivalents of anhydrous sodium acetate. The reaction mixture was refluxed for 4 h and monitored by TLC on silica gel using di­chloro­methane:ethyl acetate (9:1) as a solvent system. The separated solid was filtered, washed with cold water and dried to give the title compound. Single crystals suitable for X-ray diffraction were obtained from ethanol solution.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the title compound, C24H19N3O5S, the thia­zole ring (r.m.s. deviation = 0.012 Å) displays a planar geometry and is surrounded by three fragments, two meth­oxy­phenyl and one nitro­phenyl. The thia­zole ring is almost in the same plane as the nitro­phenyl ring, making a dihedral angle of 20.92 (6)°. The two meth­oxy­phenyl groups are perpendicular to the thia­zole ring [dihedral angles of 79.29 (6) and 71.31 (7)° and make a dihedral angle of 68.59 (7)°. The mol­ecule exists in an Z,Z conformation with respect to the C=N imine bond. In the crystal, a series of C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds, augmented by several π–π(ring) inter­actions, produce a three-dimensional architecture of mol­ecules stacked along the b-axis direction. The experimentally derived structure is compered with that calculated theoretically using DFT(B3YLP) methods.

No MeSH data available.


Related in: MedlinePlus