Local Anesthetics. I. β-Monoalkylaminoethyl Esters of Alkoxybenzoic Acids<sup>1</sup>

Pierce, J. Stanton; Salsbury, J. M.; Fredericksen, James M.

doi:10.1021/ja01259a062

Cited by 28 publications

(7 citation statements)

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“…N ‐[4‐( n ‐Butyloxy)benzoyl]benzamidine (1r): Synthesized from 4‐( n ‐butyloxy)benzoyl chloride36 (0.328 g, 1.54 mmol), benzamidine hydrochloride (0.291 g, 1.54 mmol) and NaOH (2 n , 1.93 mL). Purified by column chromatography (ethyl acetate/petroleum ether, 5:1); yield 0.355 g (78 %); colorless amorphous solid; R f = 0.58 (ethyl acetate/petroleum ether, 1:1); m.p.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Wigbers¹,

Prigge²,

Mu³

et al. 2010

Eur J Org Chem

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Keywords: Aggregation / Computational chemistry / Conformation analysis / Scanning probe microscopy / Self-assembly / Tautomerism N-Acylamidines 1a-q, which are important ligands for metal ion complexation, were easily prepared either by acylation of amidines 2 or by treatment of N-acylimidates 3 with amines. Additionally, the reaction of amidinium salts with aroyl halides in the presence of sodium hydroxide gave the aryl derivatives 1r-1ad and three azobenzene derivatives 1ae-1ag.The respective substitution pattern of these novel derivatives was selected with respect to possible steric and electronic effects in coordination reactions as well as with regard to the aggregation properties. N-Acylamidines 1 may exist as three types of tautomers, which were examined in solution by NMR spectroscopic analysis and by quantum chemical DFT and SCS-MP2-calculations for single molecules in the gas phase. Internal rotations require activation energies between

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Section: Methodsmentioning

confidence: 99%

“…N ‐[4‐( n ‐Hexyloxy)benzoyl]acetamidine (1z): Synthesized from 4‐( n ‐hexyloxy)benzoyl chloride36 (0.722 g, 3.00 mmol), acetamidine hydrochloride (0.284 g, 3.00 mmol), and NaOH (2 n , 3.00 mL); yield 0.165 g (21 %); colorless solid; m.p. 109 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Wigbers¹,

Prigge²,

Mu³

et al. 2010

Eur J Org Chem

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“…was dissolved in dry CH 2 Cl 2 (10mL), appropriate 4-alkoxybenzoic acid 7/n (see (36)(37)(38)) (1.2 eq. ), DCC (1.2 eq.)…”

Section: Methodsmentioning

confidence: 99%

Synthesis and mesomorphic behaviour of new 5‐substituted 4‐(thien‐2‐yl)phenyl benzoates

et al. 2009

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2009) Synthesis and mesomorphic behaviour of new 5-substituted 4-(thien-2-yl)phenyl benzoates, Liquid Crystals, 36:1, 61-66, 4-(5-Alkylthien-2-yl)phenyl 4-alkoxybenzoates and 4-(5-cyanothien-2-yl)phenyl 4-alkoxbenzoates are synthesised by using Pd (0) catalysed coupling reactions as key steps. The thermotropic liquid crystalline behaviour of these compounds is investigated using polarised optical microscopy (POM) and differential scanning calorimetry (DSC). Broad temperature ranges of nematic and/or smectic A mesophases are found in these compounds. The influence of the length of the alkoxy chains and molecular polarisability on the mesophase behaviours is discussed.

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“…Although one molecule of PCl 3 may provide three chlorine atoms for chlorination, there are few examples using PCl 3 for chlorination and most of them are limited to the conversion of carboxylic acids into acid chlorides. [23][24][25][26] We were interested in the potential of PCl 3 for the conversion of esters into the corresponding acid chlorides. Herein, we report a practical and simple method for the chlorination of tert-butyl esters with PCl 3 , allowing access to various acid chlorides.…”

Section: Introductionmentioning

confidence: 99%

A practical chlorination of tert-butyl esters with PCl₃ generating acid chlorides

Zhou

Yang

et al. 2020

Journal of Chemical Research

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For the first time, using PCl3, a range of tert-butyl esters is chlorinated successfully, allowing access of both aromatic acid chlorides and aliphatic acid chlorides in good yields. The method features simple reaction conditions and wide substrate scope. Various tert-butyl esters including aryl esters, alkenyl esters, and alkyl esters were tolerated well in the reaction. A plausible mechanism is proposed.

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Local Anesthetics. I. β-Monoalkylaminoethyl Esters of Alkoxybenzoic Acids¹

Cited by 28 publications

References 0 publications

Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Synthesis and mesomorphic behaviour of new 5‐substituted 4‐(thien‐2‐yl)phenyl benzoates

A practical chlorination of tert-butyl esters with PCl₃ generating acid chlorides

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Local Anesthetics. I. β-Monoalkylaminoethyl Esters of Alkoxybenzoic Acids1

Cited by 28 publications

References 0 publications

Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Synthesis, Structures, and Aggregation Properties of N‐Acylamidines

Synthesis and mesomorphic behaviour of new 5‐substituted 4‐(thien‐2‐yl)phenyl benzoates

A practical chlorination of tert-butyl esters with PCl3 generating acid chlorides

Contact Info

Product

Resources

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Local Anesthetics. I. β-Monoalkylaminoethyl Esters of Alkoxybenzoic Acids¹

A practical chlorination of tert-butyl esters with PCl₃ generating acid chlorides