Abstract
Background: Most azo dyes are synthesized by diazotization
of a primary amine, followed by conjugation with one or more electron-rich
nucleophiles. Objective: This study presents the synthesis of a new azocompound
by converting sulfamethoxazole to a diazonium salt. Methods: via
reaction with hydrochloric acid and sodium nitrite at temperatures between 0
and 5 °C, the resulting salt is then coupled with a 4-methoxyphenol reagent in
alkaline medium at the above temperatures to produce an azodye given the IUPAC
name of (4-((2-hydroxy-5-methoxyphenyl)diazenyl)-N-(5-methylisoxazol-
3yl)benzenesulfonamide). The azo dye precipitate was purified by crystallization
methods using a solvent mixture of ethanol water. Characterization was
done using different analytical methods such as IR, UV-Vis and H1-NMR in
addition to measurements of physical properties. Results: The reddish-pink
azo compound gave a maximum absorbance of 495 nm. Acid-base titrimetric
analysis was conducted to examine the chemical indicator properties of the
azo dye. Clear color differences were obtained between two spaces in the pH
range 2-12, where a reddish-pink color was obtained in the basic medium and a
yellow color in the acidic medium. Conclusions: A new azo dye successfully
presented its properties as an indicator.
of a primary amine, followed by conjugation with one or more electron-rich
nucleophiles. Objective: This study presents the synthesis of a new azocompound
by converting sulfamethoxazole to a diazonium salt. Methods: via
reaction with hydrochloric acid and sodium nitrite at temperatures between 0
and 5 °C, the resulting salt is then coupled with a 4-methoxyphenol reagent in
alkaline medium at the above temperatures to produce an azodye given the IUPAC
name of (4-((2-hydroxy-5-methoxyphenyl)diazenyl)-N-(5-methylisoxazol-
3yl)benzenesulfonamide). The azo dye precipitate was purified by crystallization
methods using a solvent mixture of ethanol water. Characterization was
done using different analytical methods such as IR, UV-Vis and H1-NMR in
addition to measurements of physical properties. Results: The reddish-pink
azo compound gave a maximum absorbance of 495 nm. Acid-base titrimetric
analysis was conducted to examine the chemical indicator properties of the
azo dye. Clear color differences were obtained between two spaces in the pH
range 2-12, where a reddish-pink color was obtained in the basic medium and a
yellow color in the acidic medium. Conclusions: A new azo dye successfully
presented its properties as an indicator.
Keywords
Sulfamethoxazole; 4-methoxy phenol; Indicator
Keywords
Sulfamethoxazole; 4-methoxy phenol; Indicator