(R)-N-(3-Meth­oxy­phen­yl)-tert-butane­sulfinamide

Xiaofei Sun; Chuan Dai; Xingzhao Tu; Wenguo Wang; Qingle Zeng

doi:10.1107/S1600536812006496

. 2012 Feb 17;68(Pt 3):o773. doi: 10.1107/S1600536812006496

(R)-N-(3-Methoxyphenyl)-tert-butanesulfinamide

Xiaofei Sun ^a, Chuan Dai ^a, Xingzhao Tu ^a, Wenguo Wang ^b, Qingle Zeng ^a,^*

PMCID: PMC3297844 PMID: 22412647

Abstract

The title compound, C₁₁H₁₇NO₂S, was obtained by the reaction of (R)-tert-butanesulfinamide with 3-methoxyphenyl bromide in toluene. In the crystal, molecules interact head-to-tail through N—H⋯O and C—H⋯O hydrogen bonds, forming one-dimensional chains parallel to the a axis.

Related literature

For the structure of the racemic title compound, see: Datta et al. (2010 ▶). For the structures of related N-arylalkanesulfinamides, see: Datta et al. (2008 ▶, 2009a ▶,b ▶). For the structures of related N-alkylalkanesulfinamides, see: Sato et al. (1975 ▶); Schuckmann et al. (1978 ▶); Ferreira et al. (2005 ▶).

Experimental

Crystal data

C₁₁H₁₇NO₂S
M _r = 227.33
Orthorhombic,
a = 7.4418 (9) Å
b = 9.7027 (12) Å
c = 16.862 (2) Å
V = 1217.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.990, T _max = 1.0
7010 measured reflections
2481 independent reflections
2062 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.092
S = 1.10
2481 reflections
204 parameters
All H-atom parameters refined
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ▶), 1029 Friedel pairs
Flack parameter: −0.02 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006496/rz2711sup1.cif

e-68-0o773-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006496/rz2711Isup4.hkl

e-68-0o773-Isup4.hkl^{(121.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006496/rz2711Isup3.cml

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
N1—H1⋯O2ⁱ	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A⋯O2ⁱ	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Science Foundation of China (grant No. 20672088), the Ministry of Human Resources and Social Security of China, the Science and Technology Bureau of Sichuan (grant No. 2011HH0016), the Opening Fund of the State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, and the Cultivating Programme for Excellent Innovation Team of Chengdu University of Technology (grant No. HY0084) for financial support.

supplementary crystallographic information

Comment

Sulfinamides, especially chiral sulfinamides, are an important class of organic compounds in modern organic chemistry, and a great number of such compounds have been synthesized. In our study on sulfinamides, we have prepared the title compound and report its crystal structure herein.

In the molecule of the title compound (Fig. 1), the N–C_aryl bond length [1.416 (3) Å] is quite similar to that found in the racemic 3-MeO-N-phenyl-tert-butanesulfinamide (1.418 (2) Å; Datta et al., 2010), and could be compared with those reported for 4-MeO-N-phenyl-tert-butanesulfinamide (1.4225 (14) Å; Datta et al., 2009a), N-phenyl-tert-butanesulfinamide (1.4083 (12) Å; Datta et al., 2009b) and other N-alkylalkanesulfinamides (1.470–1.530 Å; Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005). The crystal packing shows an intermolecular interaction through N-H···O=S hydrogen bond, forming a chain structure parallel to the a axis (Fig. 2; Table 1). In addition, the chain is enforced by an intermolecular C-H···O=S hydrogen bond as observed in the crystal packing of N-phenyladamantane-1-sulfinamide (Datta et al., 2008).

Experimental

A oven-dried ground test tube, which was equipped with a magnetic stir bar and fitted with a rubber septum, was charged with (R)-tert-butanesulfinamide (0.121 g, 1.0 mmol), Pd₂(dba)₃ (0.018 g, 0.02 mmol; dba is dibenzylideneacetone), 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.0212 g, 0.05 mmol) and NaOH (0.08 g, 2 mmol). The vessel was evacuated and backfilled with argon three times, then 3-methoxyphenyl bromide (1.3 mmol), toluene (10 ml) and degassed water (0.3 mL) were added via syringe. The solution was stirred at 90°C for 20 h. The reaction mixture was then cooled to room temperature, quenched by water, and extracted with ethyl acetate (20 mL) for twice. The organic layer was combined, and dried over anhydrous sodium sulfate and filtrated. The filterate was condensed under vacuum. The residual was purified with silica gel column chromatography with a solution of petroleum ether and ethyl acetate (5:1 v:v) as eluent. A test tube containing the eluate was covered with a piece of filter paper and placed motionless at room temperature, and a single crystal was cultured in the bottom of the test tube. Yield: 0.186 g, 82%. Spectroscopic analysis: ESI-MS (negative mode), m/z = 226 [M-H]-. FTIR (KBr) (cm^-1): 3456, 3273, 3112, 3076, 2966, 1584, 1519, 1246, 1186, 1113, 1068, 875, 795, 751. ¹H NMR (300 MHz, CDCl₃), δ (ppm): 7.16 (t, J = 8.2 Hz, 1H), 5.60-5.55 (m, 3H), 5.34 (s, 1H), 3.78(s, 3H), 1.33 (s, 9H). ¹³C NMR (300 MHz, CD₃OD), δ (ppm): 160.2, 143.5, 129.8, 110.1, 107.9, 103.5, 56.3, 54.9, 22.3. [α]D = -2.6 (c 0.05, ethyl acetate).