2-Amino-4-tert-butyl-5-(4-chloro­benz­yl)thia­zole

Yong-Tao Wang; Lin Xia; Ai-Xi Hu; Gao Cao; Juan-Juan Xu

doi:10.1107/S160053680803715X

. 2008 Nov 13;64(Pt 12):o2350. doi: 10.1107/S160053680803715X

2-Amino-4-tert-butyl-5-(4-chlorobenzyl)thiazole

Yong-Tao Wang ^a, Lin Xia ^a, Ai-Xi Hu ^a,^*, Gao Cao ^a, Juan-Juan Xu ^a

PMCID: PMC2959929 PMID: 21581324

Abstract

In the title compound, C₁₄H₁₇ClN₂S, the dihedral angle between the planes of the thiazole and chlorophenyl rings is 88.86 (3)°. In the crystal, inversion dimers occur, linked by pairs of N—H⋯N hydrogen bonds.

Related literature

For background on 2-amino-4-arylthiazoles and their wide-ranging antifungal activities, see: Hu et al. (2007a ▶); Marcantonio et al. (2002 ▶). For related structures, see: Cao et al. (2007 ▶); He et al. (2006 ▶); Hu et al. (2007b ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₇ClN₂S
M _r = 280.81
Monoclinic,
a = 21.1775 (13) Å
b = 5.8544 (4) Å
c = 22.8193 (14) Å
β = 98.5480 (10)°
V = 2797.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.41 mm⁻¹
T = 173 (2) K
0.48 × 0.29 × 0.17 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.829, T _max = 0.934
6230 measured reflections
2705 independent reflections
2187 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.120
S = 1.06
2705 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803715X/sg2282sup1.cif

e-64-o2350-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803715X/sg2282Isup2.hkl

e-64-o2350-Isup2.hkl^{(132.9KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.88	2.24	3.032 (2)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was funded by the National Key Technology R&D Program, China (NO: 2006 BAE01A01–4).

supplementary crystallographic information

Comment

2-Amino-4-arylthiazoles are an important class of heterocyclic compounds in the field of organic pharmaceutial chenistry (Hu et al., 2007a, Marcantonio et al.,2002). Because of their wide-ranging antifungal activities, The structure of 2-amino-4-arylthiazoles were reported before (Cao,et al.,2007, He et al.,2006, Hu et al.,2007b, Xu, et al.,2007). Herein we report the synthesis and crystal structure of 2-amino-4-tert-butyl-5-(4- chlorobenzyl)thiazole(I). The dihedral angle between the planes of thiazole and the chlorophenyl ring is 88.86 °. The molecules are linked by N—H···N hydrogen bonds.

Experimental

0.01 mol of 1-(4-Chlorophenyl)-4,4-dimethylpentan-3-one was dissolved in 100 ml e thanol and the mixture was stirred and heated to reflex. 0.012 mol of cupric chloride was added by dropwise. The reaction was monitored by TLC, after it finished, filtered the mixture and concentrated in vacuo. The residue was taken up in dichloromethane, washed with 10% hydrochloric acid, then washed with water until the solution was neutral, dried and concentrated in vacuo to give 4-chloro-1-(4-chlorophenyl)-4,4-dimethylpentan -3-one, yield 87%. Then a solution with 0.005 mol of thiurea and 0.005 mol of 4-chloro-1-(4-chlorophenyl)-4,4-dimethylpentan -3-one in 50 ml of ethanol was refluxed for 10 h. After finishing the reaction, added 10 ml ammonia and continus to stir the sulution 2 h. Then the solution was cooled and the precipitate formed was filtered out, dried, giving white crystals of title compound,yield 73.8%. The crystals for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.