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Journals / TOJSAT / 2012 / Cilt: 2 Sayı: 4

Novel Chiral Compound: (R) and (S) 1-(2-Benzyloxy-3-Methoxyphenyl)-2,2,2Trichloroethyl Benzensulfonate, Synthesys and characterization

Mohammed Hadi AL-DOUH
Journal
TOJSAT
Pages
59–67
Publication Date
2016-07-23
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The complete assignments of 4 were made using 1D and 2D NMR

📌 3 Key Takeaways

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Objective & Hypothesis:The reaction between benzimidazole 1 and benzenesulfonyl chloride 2 in dichloromethane (DCM) at 45 oC for 10 hr in the presence of dimethyl aminopyridine (DMAP) as a catalyst was expected to obtain 2(2-benzyloxy-3-methoxyphenyl)-1-(phenylsulfonyl)-1H-benzimidazole, 3.
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Key Findings & Data:Unfortunately, a novel chiral compound (R) and (S) 1-(2-benzyloxy-3-methoxyphenyl)-2,2,2-trichloroethyl benzenesulfonate 4 was obtained as a single crystal (59% yield) with melting point of 58.4 °C.
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Conclusion & Impact:The complete assignments of 4 were made using 1D and 2D NMR
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:1 H NMR · 13C NMR · 2D NMR

Abstract

The reaction between benzimidazole 1 and benzenesulfonyl chloride 2 in dichloromethane (DCM) at 45 oC for 10 hr in the presence of dimethyl aminopyridine (DMAP) as a catalyst was expected to obtain 2(2-benzyloxy-3-methoxyphenyl)-1-(phenylsulfonyl)-1H-benzimidazole, 3. Unfortunately, a novel chiral compound (R) and (S) 1-(2-benzyloxy-3-methoxyphenyl)-2,2,2-trichloroethyl benzenesulfonate 4 was obtained as a single crystal (59% yield) with melting point of 58.4 °C. However, the mechanism of this reaction still is under investigation. The molecular structure of this compound was confirmed by FTIR, HRMS, X–Ray crystallography, 1D and 2D NMR spectroscopy. The crystal of 4 is in the monoclinic space group P21/c with a = 8.1638 (1) Å, b = 8.8536 (1) Å, c = 30.7221 (5) Å, β = 90.670 (1)o, Dcalc = 1.501 μg m-3, V = 2220.41 (5) Å and Rint = 0.059. The complete assignments of 4 were made using 1D and 2D NMR including APT, DEPT–135, COSY, HMQC and HMBC in CDCl3. 3 and R = 0.059. The complete assignments of 4 were made using 1D and 2D NMR

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Cite This Article

AL-DOUH, M. H. (2016). Novel Chiral Compound: (R) and (S) 1-(2-Benzyloxy-3-Methoxyphenyl)-2,2,2Trichloroethyl Benzensulfonate, Synthesys and characterization. TOJSAT, Cilt: 2 Sayı: 4, 59–67. https://ajindex.com/articles/1008746

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References (3)

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