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Crystal structures of N -[(4-phenyl ­ thia ­ zol-2-yl)carbamo ­ thio ­ yl]benzamide and N -{[4-(4-bromo ­ phen ­ yl)thia ­ zol-2-yl]carbamo ­ thio ­ yl}benzamide from synchrotron X-ray diffraction

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ABSTRACT

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamo­thio­yl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thia­zole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thia­zol-2-ylcarbamo­thio­yl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromo­phenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol­ecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] inter­actions.

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Synthesis of new thio­urea derivatives (I) and (II).
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fig5: Synthesis of new thio­urea derivatives (I) and (II).

Mentions: Benzoyl chloride (0.60 ml, 0.73 g, 5.19 mmol) was added over 5 min to a freshly prepared solution of NH4SCN (0.39 g, 5.19 mmol) in acetone (40 ml), and the mixture was heated under reflux for 15 min. After heating, the appropriate 4-aryl­thia­zol-2-amine (4.33 mmol) in acetone (10 ml) was added. The mixture was heated again under reflux for 2 h (Fig. 5 ▸). Then excess cracked ice was added with vigorous stirring. The resulting solid was collected and liberally washed with water. These compounds were isolated as pale-yellow crystalline solids in 41% and 45% yield for the 4-phenyl (I) and 4-(4-bromo­phen­yl) (II) derivatives, respectively. Single crystals of the products were obtained by slow crystallization from N,N-di­methyl­formamide solution.


Crystal structures of N -[(4-phenyl ­ thia ­ zol-2-yl)carbamo ­ thio ­ yl]benzamide and N -{[4-(4-bromo ­ phen ­ yl)thia ­ zol-2-yl]carbamo ­ thio ­ yl}benzamide from synchrotron X-ray diffraction
Synthesis of new thio­urea derivatives (I) and (II).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120721&req=5

fig5: Synthesis of new thio­urea derivatives (I) and (II).
Mentions: Benzoyl chloride (0.60 ml, 0.73 g, 5.19 mmol) was added over 5 min to a freshly prepared solution of NH4SCN (0.39 g, 5.19 mmol) in acetone (40 ml), and the mixture was heated under reflux for 15 min. After heating, the appropriate 4-aryl­thia­zol-2-amine (4.33 mmol) in acetone (10 ml) was added. The mixture was heated again under reflux for 2 h (Fig. 5 ▸). Then excess cracked ice was added with vigorous stirring. The resulting solid was collected and liberally washed with water. These compounds were isolated as pale-yellow crystalline solids in 41% and 45% yield for the 4-phenyl (I) and 4-(4-bromo­phen­yl) (II) derivatives, respectively. Single crystals of the products were obtained by slow crystallization from N,N-di­methyl­formamide solution.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamo­thio­yl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thia­zole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thia­zol-2-ylcarbamo­thio­yl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromo­phenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol­ecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] inter­actions.

No MeSH data available.