Preparation of Some 2-(Methoxyphenyl)-2H-benzotriazoles and the Corresponding Hydroxyphenyl Compounds

1987 ◽  
Vol 40 (10) ◽  
pp. 1663 ◽  
Author(s):  
J Rosevear ◽  
JFK Wilshire
Keyword(s):  
Acetic Acid ◽  
Good Yield ◽  
Hydrobromic Acid ◽  
Methoxy Group ◽  
Methylene Chloride ◽  
Thiourea Dioxide ◽  
Boron Tribromide

The reaction of several substituted o- nitronitrosobenzenes with O- and p- anisidine , and 2,4- dimethoxyaniline in acetic acid gives in good yield the corresponding enitroazobenzenes which are readily reduced with thiourea dioxide ( formamidinesulfinic acid) to the corresponding 2-(methoxypheny1)-2H-benzotriazoles, demethylation of which furnished the corresponding 2- (hydroxypheny1)-2H-benzotriazoles. Demethylation of the dimethoxy derivatives was best accomplished with boron tribromide in methylene chloride, the methoxy group located ortho to the benzotriazole ring being demethylated more readily than is the para-methoxy group. The reaction of enitroazobenzenes containing a methoxy group with hydrobromic acid in acetic acid results in cleavage of the azo bond and also partial bromination to give o- nitroaniline and some of its brominated derivatives.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

scholarly journals Thin layer chromatographic compatibility study in preformulation of new transdermal therapeutic systems

2020 ◽  
Vol 66 (1) ◽  
pp. 23-29
Author(s):  
Octavia-Laura Moldovan ◽  
Diana-Nicoleta Brihan ◽  
Nicoleta Todoran ◽  
Aura Rusu
Keyword(s):  
Acetic Acid ◽  
Thin Layer ◽  
Mobile Phase ◽  
Glacial Acetic Acid ◽  
Methylene Chloride ◽  
Hydroxyethyl Cellulose ◽  
Compatibility Study ◽  
Chemical Interactions ◽  
Miconazole Nitrate ◽  
Active Substances

AbstractObjective: The compatibility of four binary active substances combinations adapalene – levofloxacin (ADP-LFX), adapalene – miconazole nitrate (ADP-MCZ), levofloxacin – meloxicam (LFX-MLX) and levofloxacin – miconazole nitrate (LFX-MCZ) was analysed to be comprised in new transdermal therapeutic systems. Also, the compatibility of selected active substances and four polymeric excipients (hydroxypropyl methyl-cellulose - HPMC 15000, hydroxypropyl methylcellulose - HPMC E5, ethyl cellulose - EC 10, and hydroxyethyl cellulose – HEC) was studied.Methods: Thin layer chromatographic method (TLC) and four selected mobile phases were used. On the plate (in situ) were obtained the binary combinations (active substances and active substance-polymer).Results: A good compatibility of ADP-LFX was found using ammonia : methanol : acetonitrile : methylene chloride 2:4:1:4 mobile phase. Using chloroform : acetone : glacial acetic acid 34:4:3 on the chromatogram of ADP-MCZ, only ADP spots appeared but without changes in the shape of the spots and Rf values. Any modifications of LFX and MLX spots (from LFX-MLX mixture) had been observed using toluene : glacial acetic acid : methanol 11:1:0.5 mobile phase, although LFX spots have remained on the baseline. Only LFX spots were visible from LFX-MLX and LFX-MCZ mixtures (ammonia : methanol : acetonitrile : methylene chloride 2:4:1:4 mobile phase). Distinctive spots were observed for ADP, LFX and MLX with variable results from no chemical interactions to limited chemical interactions when the compatibility with polymers was verified.Conclusions: ADP-LFX and LFX-MLX mixtures were found to be compatible. ADP with HPMC polymers and LFX with HPMC E5 and HEC had presented excellent compatibility; for the other binary combinations, different analytical methods will be necessary.

Determination of Carbaryl Residues in Honey Bees

1965 ◽  
Vol 48 (4) ◽  
pp. 771-774
Author(s):  
D P Johnson ◽  
H A Stansbury
Keyword(s):  
Aqueous Solution ◽  
Acetic Acid ◽  
Quantitative Determination ◽  
Honey Bees ◽  
Methylene Chloride ◽  
Hydrolysis Product ◽  
Separate Analysis ◽  
Yellow Substance ◽  
Hydrolysis Of

Abstract A method has been developed for detecting residues of carbaryl (1-naphthyl methylcarbamate) as well as its hydrolysis product, 1-naphthol, in dead bees. The method is based on extraction of the bees with benzene, followed by a cleanup involving liquid partitioning and chromatography on Florisil. The quantitative determination involves hydrolysis of carbaryl to 1-naphthol and coupling of the latter with p-nitrobenzenediazonium fluoborate in acetic acid to form a yellow substance. For separate analysis, free 1-naphthol is separated from methylene chloride into a basic aqueous solution. The sensitivity of the method is about 0.1 ppm; recoveries averaged 85.6 ± 6.6% for 1- naphthol and 83.8 ± 2.7% for carbaryl.

The Synthesis of Zinquin Ester and Zinquin Acid, Zinc(II)-Specific Fluorescing Agents for Use in the Study of Biological Zinc(II)

1996 ◽  
Vol 49 (5) ◽  
pp. 561 ◽  
Author(s):  
IB Mahadevan ◽  
MC Kimber ◽  
SF Lincoln ◽  
ERT Tiekink ◽  
AD Ward ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Crystal Structures ◽  
Electrophilic Substitution ◽  
Ethyl Acrylate ◽  
Heck Coupling ◽  
Ethyl Bromoacetate ◽  
Reaction Conditions ◽  
Bromo Derivative ◽  
Boron Tribromide

The syntheses of Zinquin ester [ethyl [2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate] and the corresponding acid, both of which are zinc(II)-specific fluorophores , are described. 6-Methoxy-2-methyl-8-(p- tolylsulfonylamino ) quinoline (2) can be demethylated , with boron tribromide, to form either the expected phenol or a mixture of the phenol and the corresponding 5-bromo derivative depending upon the reaction conditions. These compounds react with ethyl bromoacetate to give the corresponding esters, as well as the 5-ethoxycarbonyl derivative formed by electrophilic substitution. Halogenation of the sulfonamide (2) occurs readily at the 5-position. The 5-iodo product undergoes a Heck coupling with ethyl acrylate . The crystal structures of ethyl [5-ethoxycarbonylmethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetate and [5-carboxymethyl-2-methyl-8-(p- tolylsulfonylamino )-6-quinolyloxy]acetic acid are described.

Synthesis and Antimicrobial Evaluation of Some New 2-(6-Oxo-5,6- dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides

2010 ◽  
Vol 65 (5) ◽  
pp. 617-624 ◽  
Author(s):  
Prajwal L. Lobo ◽  
Boja Poojary ◽  
Kumsi Manjunatha ◽  
Nalilu Suchetha Kumari
Keyword(s):  
Acetic Acid ◽  
Antifungal Activity ◽  
Spectral Data ◽  
Good Yield ◽  
Antibacterial And Antifungal Activity ◽  
Acid Media ◽  
Antimicrobial Evaluation ◽  
Antibacterial And Antifungal

A series of 2-(6-oxo-5,6-dihydro[1,3]thiazolo[3,2-b]-2-aryloxymethyl-1,2,4-triazol-5-yl)-Narylacetamides 6 were synthesized in good yield by condensing 5-aryloxymethyl-4H-1,2,4-triazole- 3-thiol 5 with various substituted N-phenyl-maleimides in acetic acid media. The newly synthesized compounds were characterized by spectral data and tested for their in vitro antibacterial and antifungal activity against a variety of microorganisms.

IX.—The Synthesis of 8-Bromo-3-methoxyfluoranthene.

1969 ◽  
Vol 68 (2) ◽  
pp. 127-137
Author(s):  
Neil Campbell ◽  
Naim M. Hasan
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acids ◽  
Good Yield ◽  
Related Compounds

SummaryA second method for the synthesis of 8-bromo-3-methoxyfluoranthene from 2-bromo-7-methoxyfluorene is described. The autoxidation of fluorene derivatives including the 9-carboxylic acids and of related compounds, particularly 4-α-cyanobenzyl-7−oxo-7H-benz[de]anthracene, is discussed. Unsuccessful attempts to prepare 3-bromofluorene-9-acetic acid in good yield are reported.

Fused Supracyclopentadienyl Ligand Precursors. Synthesis, Structure, and Some Reactions of 1,3-Diphenylcyclopenta[l]phenanthrene-2-one, 1,2,3-Triphenylcyclopenta[l]phenanthrene-2-ol, 1-Chloro-1,2,3-triphenylcyclopenta[l]phenanthrene, 1-Bromo-1,2,3-triphenylcyclopenta[l]phenanthrene, and 1,2,3-Triphenyl-1H-cyclopenta[l]phenanthrene

2006 ◽  
Vol 59 (2) ◽  
pp. 135 ◽  
Author(s):  
Glen D. Dennis ◽  
David Edwards-Davis ◽  
Leslie D. Field ◽  
Anthony F. Masters ◽  
Thomas Maschmeyer ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Good Yield ◽  
Photochemical Reaction ◽  
Subsequent Reaction ◽  
X Ray ◽  
X Ray Crystallography ◽  
Independent Synthesis ◽  
Ligand Precursors

The photochemical reaction of 1,3-diphenylcyclopenta[l]phenanthrene-2-one 5 (phencyclone) with oxygen in acetone leads to the formation of 1,2,3-trihydro-1,2,3-triphenylcyclo-penta[l]phenanthrene 7 (9,10-dibenzoylphenanthrene) along with a trace of the lactone 1,4-diphenylcyclo-3-pyran[l]phenanthrene-2-one 8. An independent synthesis of 8 was achieved by the reaction of 5 with FeCl3 in CHCl3. The treatment of 5 with phenyllithium yields 1,2,3-triphenylcyclopenta[l]phenanthrene-2-ol 9-OH in good yield. Subsequent reaction of 9-OH with SOCl2 or SOBr2 in pyridine leads to the formation of the halo-analogues 1-chloro-1,2,3-triphenylcyclopenta[l]phenanthrene 9-Cl and 1-bromo-1,2,3-triphenylcyclopenta[l]phenanthrene 9-Br, respectively. Treatment of 9-OH with HBr in acetic acid affords the rearranged product 1,1,3-triphenylcyclopenta[l]phenanthrene-2-one 10 with a trace of 9-Br. Treatment of 9-Cl or 9-Br with zinc in acetic acid affords 1,2,3-tri-phenyl-1H-cyclopenta[l]phenanthrene 9-H. 9,10-Phenanthrenediylbis(phenyl)methanone 7 is formed in good yield upon treatment of 9-OH with HI in acetic acid followed by heating with H2PO4. Compounds 7, 8, 9-Cl, 9-Br, and 10 have been structurally characterized using X-ray crystallography.

THE REACTION OF CHLORAL WITH HALOBENZENES AND WITH 2,4-DICHLOROPHENOL: SYNTHESIS OF HALOGENATED ETHYLBENZENES AND OF α-METHOXYPHENYLACETIC ACIDS

1966 ◽  
Vol 44 (5) ◽  
pp. 575-582 ◽  
Author(s):  
Wilkins Reeve ◽  
John P. Mutchler ◽  
Charles L. Liotta
Keyword(s):  
Carbon Disulfide ◽  
Potassium Hydroxide ◽  
Methoxy Group ◽  
Methylene Chloride ◽  
Aluminium Chloride ◽  
Molar Ratio ◽  
Side Chain ◽  
New Compounds ◽  
Hydroxy Groups

The Friedel–Crafts reaction of chloral with aromatic compounds to form aryltrichloromethylcarbinols is reviewed. The molar ratio of aluminium chloride to chloral is critical and varies from 0.15 to 2.0 depending on the solvent, steric considerations, and the reactivity of the aromatic ring. The reaction has been used to prepare several new compounds with carbon disulfide or excess aromatic compound as the solvent. From 2,4-dichlorophenol, an o-hydroxy-α-trichloromethylbenzyl alcohol is obtained. Both the phenolic and side-chain hydroxy groups of this alcohol are methylated with equal ease by dimethyl sulfate.It has now been found that changing the solvent from carbon disulfide to methylene chloride results in the hydroxy group of the initial carbinol also being replaced by chlorine. This role of the solvent in controlling the course of the reaction has not been observed previously.The trichloromethylcarbinols are converted into α-methoxy acids by treatment with methanolic potassium hydroxide. Sodium in liquid ammonia removes the α-methoxy group, as well as the halogens, from 3,5-dichloro-α,2-dimethoxyphenylacetic acid.

Synthesis, Characterization and Biological Studies of Some Bioactive Thiazolotriazole Derivatives

2010 ◽  
Vol 65 (12) ◽  
pp. 1509-1515 ◽  
Author(s):  
Manjunatha Kumsi ◽  
Boja Poojary ◽  
Prajwal Lourdes Lobo ◽  
Nalilu Suchetha Kumari ◽  
Anoop Chullikana
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Good Yield ◽  
Sodium Acetate ◽  
Aromatic Aldehydes ◽  
Antimicrobial Activities ◽  
One Pot ◽  
Biological Studies ◽  
Elemental Analyses

The key precursor rac-2-(4-isobutylphenyl)ethyl-1,2,4-triazole-5-thione (3) was synthesized in good yield from Ibuprofen (1). One-pot three-component reactions of 3 with 5-aryl-furan-2-carboxaldehydes/ substituted aromatic aldehydes and monochloroacetic acid in acetic acid in the presence of acetic anhydride and anhydrous sodium acetate afforded substituted thiazolo[3,2-b][1,2,4]triazole derivatives 4 and 5. The structures of the newly synthesized compounds were elucidated by elemental analyses and spectral data. The compounds were tested for their in-vitro antimicrobial activities.

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