Synthetic Antimalarials. The Preparation of Certain Derivatives of Sulfanilamide<sup>1</sup>

Drake, Nathan L.; Eaker, Charles M.; Garman, John A.; Hamlin, K. E.; Hayes, Robert A.; Haywood, Stuart T.; Peck, Richard M.; Preston, Robert K.; Sterling, John D.; Hook, J. O. Van.; Walton, Edward

doi:10.1021/ja01212a070

Cited by 7 publications

(4 citation statements)

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“…[4-H−Ar‘]Li (4-H−Ar‘ = Ar‘ = C 6 H 3 -2,6-(C 6 H 3 -2,6- i Pr 2 ) 2 ), (Ar‘SnCl) 2 , and [3,5- i Pr 2 −Ar*]Li (3,5- i Pr 2 −Ar* = 3,5- i Pr 2 −C 6 H-2,6-(C 6 H 2 -2,4,6- i Pr 3 ) 2 ), were prepared according to literature procedures. 1-Iodo-2,6-dibromo-4- tert -butylbenzene and 2,6-dichloro-4-trimethylsilylbenzene were also synthesized as described in the literature. n BuLi (2.5 M solution in hexanes), anhydrous SnCl 2 , LiBH 4 , LiNMe 2 , i Bu 2 AlH (DIBAL), BH 3 ·THF (1.0 M solution in THF), and 3,5-dichloroanisole were purchased from commercial sources and used as received.…”

Section: Methodsmentioning

confidence: 99%

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System

et al. 2007

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A series of symmetric divalent Sn(II) hydrides of the general form [(4-X-Ar')Sn(mu-H)]2 (4-X-Ar' = C6H2-4-X-2,6-(C6H3-2,6-iPr2)2; X = H, MeO, tBu, and SiMe3; 2, 6, 10, and 14), along with the more hindered asymmetric tin hydride (3,5-iPr2-Ar*)SnSn(H)2(3,5-iPr2-Ar*) (16) (3,5-iPr2-Ar* = 3,5-iPr2-C6H-2,6-(C6H2-2,4,6-iPr3)2), have been isolated and characterized. They were prepared either by direct reduction of the corresponding aryltin(II) chloride precursors, ArSnCl, with LiBH4 or iBu2AlH (DIBAL), or via a transmetallation reaction between an aryltin(II) amide, ArSnNMe2, and BH3.THF. Compounds 2, 6, 10, and 14 were obtained as orange solids and have centrosymmetric dimeric structures in the solid state with long Sn...Sn separations of 3.05 to 3.13 A. The more hindered tin(II) hydride 16 crystallized as a deep-blue solid with an unusual, formally mixed-valent structure wherein a long Sn-Sn bond is present [Sn-Sn = 2.9157(10) A] and two hydrogen atoms are bound to one of the tin atoms. The Sn-H hydrogen atoms in 16 could not be located by X-ray crystallography, but complementary Mössbauer studies established the presence of divalent and tetravalent tin centers in 16. Spectroscopic studies (IR, UV-vis, and NMR) show that, in solution, compounds 2, 6, 10, and 14 are predominantly dimeric with Sn-H-Sn bridges. In contrast, the more hindered hydrides 16 and previously reported (Ar*SnH)2 (17) (Ar* = C6H3-2,6-(C6H2-2,4,6-iPr3)2) adopt primarily the unsymmetric structure ArSnSn(H)2Ar in solution. Detailed theoretical calculations have been performed which include calculated UV-vis and IR spectra of various possible isomers of the reported hydrides and relevant model species. These showed that increased steric hindrance favors the asymmetric form ArSnSn(H)2Ar relative to the centrosymmetric isomer [ArSn(mu-H)]2 as a result of the widening of the interligand angles at tin, which lowers steric repulsion between the terphenyl ligands.

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Section: Methodsmentioning

confidence: 99%

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System

et al. 2007

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“…Major chemicals were obtained from Aldrich. 1-Iodo-2,6-dibromobenzene and 1-iodo-2,6-dibromo-4- tert -butylbenzene were prepared using standard procedures of functional group transformations; starting materials were sulfanilamide (or 2,6-dibromoaniline) and tert -butylbenzene, respectively. − The vacuum lines and glovebox are described elsewhere …”

Section: Methodsmentioning

confidence: 99%

Biphenylene Dimer. Molecular Fragment of a Two-Dimensional Carbon Net and Double-Stranded Polymer

et al. 1996

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Biphenylene dimers, which may be considered as "macrocyclic" 2 × 2 fragments of net 1 and dimeric fragments of a double-stranded polymer, 5, are prepared. X-ray crystallography on two polymorphs of the dimer 9 reveals that its bond alternation is analogous to that in biphenylene; the tetraphenylene part of 9 has approximately C 2h symmetry with a small dihedral angle (<12°) between the benzene rings in the adjacent biphenylenes. Cyclic voltammetry of 9 gives two reversible waves corresponding to a radical anion and a dianion; the lithium and potassium salts of these anions, 9 •-,M + (M ) Li, K) and 9 2-,2M + (M ) Li, K), were generated and characterized by ESR, NMR, and UV-vis spectroscopies. The spectral data for the dianions are compatible with classical structures; no evidence for "in-plane aromaticity" is found. For polymer 5, a localized band and large density of states near the Fermi level are found, using extended Hu ¨ckel theory calculations.

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“…Based on MS n data, molecular formulae generated by the Formula Predictor software (Shimadzu), and results from the SciFinder and ChemSpider databases, the proposed identification of the chlorinated product is 4-amino-(5-chloro-4,6-dimethyl-2-pyrimidinyl)-benzenesulfonamide (C 12 H 13 N 4 O 2 SCl). This compound was previously synthesized by Drake et al by coupling N-acetylsulfanilyl chloride to the amine in pyridine followed by hydrolysis with sodium hydroxide [ 23 ]. This reaction involved a 2-hour incubation time at 60–70°C temperatures to achieve a 47% yield.…”

Section: Resultsmentioning

confidence: 99%

The Fate of Sulfamethazine in Sodium-Hypochlorite-Treated Drinking Water: Monitoring by LC--IT-TOF

Melton

Brown

2012

International Journal of Medicinal Chemistry

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Pharmaceutical compounds represent a rapidly emerging class of environmental contaminants. Such compounds were recently classified by the U.S. Geological Survey, including several antibiotics. An LC-MS/MS screening method for the top five antibiotics in drinking water was developed and validated using a Shimadzu LC-MS-IT-TOF. The separation was performed using a Waters Acquity UPLC BEH C18 column with a gradient elution. Sulfamethazine was exposed to conditions intended to mimic drinking water chlorination, and samples were collected and quenched with excess sodium sulfite. Kinetics of sulfamethazine degradation was followed as well as the formation of the major chlorinated byproduct (m/z 313). For the screening method, all five antibiotic peaks were baseline resolved within 5 minutes. Additionally, precision and accuracy of the screening method were less than 15%. Degradation of sulfamethazine upon exposure to drinking water chlorination occurred by first order kinetics with a half-life of 5.3 × 104 min (approximately 37 days) with measurements starting 5 minutes after chlorination. Likewise, the formation of the major chlorinated product occurred by first order kinetics with a rate constant of 2.0 × 10−2. The proposed identification of the chlorinated product was 4-amino-(5-chloro-4,6-dimethyl-2-pyrimidinyl)-benzenesulfonamide (C12H13N4O2SCl) using MSn spectra and databases searches of SciFinder and ChemSpider.

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Synthetic Antimalarials. The Preparation of Certain Derivatives of Sulfanilamide¹

Cited by 7 publications

References 1 publication

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System

Biphenylene Dimer. Molecular Fragment of a Two-Dimensional Carbon Net and Double-Stranded Polymer

The Fate of Sulfamethazine in Sodium-Hypochlorite-Treated Drinking Water: Monitoring by LC--IT-TOF

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Synthetic Antimalarials. The Preparation of Certain Derivatives of Sulfanilamide1

Cited by 7 publications

References 1 publication

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]2 (Ar = Terphenyl) System

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]2 (Ar = Terphenyl) System

Biphenylene Dimer. Molecular Fragment of a Two-Dimensional Carbon Net and Double-Stranded Polymer

The Fate of Sulfamethazine in Sodium-Hypochlorite-Treated Drinking Water: Monitoring by LC--IT-TOF

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Synthetic Antimalarials. The Preparation of Certain Derivatives of Sulfanilamide¹

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System

Isomeric Forms of Heavier Main Group Hydrides: Experimental and Theoretical Studies of the [Sn(Ar)H]₂ (Ar = Terphenyl) System