2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidoprop­yl)-N,N′-(propane-1,3-di­yl)dibenzene­sulfonamide

Yu-Xia Wang; Peng-Fei Cheng; Chao-Jie Wang

doi:10.1107/S1600536808036003

. 2008 Nov 8;64(Pt 12):o2289. doi: 10.1107/S1600536808036003

2,2′,4,4′,6,6′-Hexamethyl-N-(3-phthalimidopropyl)-N,N′-(propane-1,3-diyl)dibenzenesulfonamide

Yu-Xia Wang ^a,^*, Peng-Fei Cheng ^a, Chao-Jie Wang ^a

PMCID: PMC2960108 PMID: 21581267

Abstract

In the title compound, C₃₂H₃₈N₃O₆S₂, an intermediate in the synthesis of polyamine drugs, the dihedral angle between the phenyl rings of the two 2,4,6-trimethylbenzenesulfonyl groups is 27.1 (3)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O hydrogen bonds, thereby forming an infinite one-dimensional chain propagating along [010].

Related literature

Polyamines are essential growth factors for cells, existing mainly as polycations at physiological pH, see: Cullis et al. (1999 ▶); Seiler et al. (1996 ▶); Tsen et al. (2008 ▶).

Experimental

Crystal data

C₃₂H₃₉N₃O₆S₂
M _r = 625.78
Monoclinic,
a = 32.042 (3) Å
b = 9.9782 (8) Å
c = 25.105 (2) Å
β = 127.917 (1)°
V = 6332.1 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 (2) K
0.18 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.962, T _max = 0.973
17128 measured reflections
6212 independent reflections
4574 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.219
S = 1.09
6212 reflections
388 parameters
44 restraints
H-atom parameters constrained
Δρ_max = 0.80 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036003/hb2835sup1.cif

e-64-o2289-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036003/hb2835Isup2.hkl

e-64-o2289-Isup2.hkl^{(304.2KB, 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
N3—H3B⋯O5ⁱ	0.86	2.53	3.192 (4)	134

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

supplementary crystallographic information

Comment

Polyamines are essential growth factors for cells, which exist mainly as polycations at physiological pH (Cullis et al., 1999; Seiler et al., 1996; Tsen et al., 2008). As part of our studies in this area, herein we report the synthesis and structure of the title compound, (I).

The compound (I) consists of a polyamine chain with two 2,4,6-trimethylbenzenesulfonyl group acting as protecting groups (Fig. 1). In the structure of (I), the two phenyl ring of two 2,4,6-trimethylbenzenesulfonyl group are nonparallel due to steric hindrance, charactrtized by a dihedral angel of 27.1 (3) °.

In the crystal, molecules are linked through intermolecular N–H···O hydrogen bonds to construct an infinite one-dimensional chain (Fig. 2 and Table 1).

Experimental

Propane-1,3-diamine 1.85 g (25 mmol) was dissolved in 2 M sodium hydroxide and the solution was cooled to 0 °C, a solution of 2,4,6-trimethylbenzenesulfonyl chloride 10.9 g (50 mmol) in CH₂Cl₂ (25 ml) was added dropwise. The reaction mixture was then stirred at room temperture for 18 h. The organic phase was separated from the aqueous phase and washed with 0.5 M HCl solution and brine. The CH₂Cl₂ layer was dried over sodium sulfate, filtered and the solvent removed in vacuo, and the residue purified by chromatography.

A mixture of N¹,N³—Bis(mesitylenesulfonyl)-1,3-propyl-diamine 1.05 g (2.33 mmol) and 60% NaH (5.35 mmol, 0.22 g) in DMF 20 ml was stirred at 0 °C for 0.5 h, then warmed to room temperature for 0.5 h. N-(3-bromopropyl)phthalimide 1.57 g (5.82 mmol) was added and the reaction mixture was stirred at 40 °C for 4 h, then EtoH (2.5 ml) and water (5 ml) were added, the solvent was removed in vacuo at 80 °C, the residue was dissolved in CHCl₃ and washed with water, the organic layer was dried over anhydrous sodium sulfate and filtered, then concentrated in vacuo, the residue was purified by chromatography. Colorless rod crystal of (I) were obtained.