The title compound, propyl gallate (III), is an important substance popularly used in the food, cosmetic and pharmaceutical industries. Current chemical syntheses of this compound are based on the acylation supported by thionyl chloride, DIC/DMAP or Fischer esterification using a range of homogenous and heterogenous catalysts. In this paper, an efficient, green, straightforward, and economical method for synthesizing propyl gallate using potassium hydrogen sulfate, KHSO4, as the heterogenous acidic catalyst has been developed for the first time. In addition, this paper provides a comprehensive spectral dataset for the title compound, especially the new data on DEPT and 2D NMR (HSQC and HMBC) spectra which are not currently available in the literature.
Afatinib is a 4-anilinoquinazoline tyrosine kinase inhibitor (TKI) in the form of a dimaleate salt which is indicated for the treatment of locally advanced or metastatic non-small cell lung cancer (NSCLC). The most scalable route for the synthesis of this drug was reported in two Boehringer Ingelheim patents, in which the title compound, 4,7-dichloro-6-nitroquinazoline (IV), is an important intermediate. Compound IV is also present in a number of synthetic pathways for various 4,7-disubstituted quinazoline derivatives displaying high therapeutic potential. However, no detailed characterization of this popular compound has been reported, possibly due to its high instability. In this paper, IV was prepared in an overall yield of 56.1% by a 3-step process (condensation, nitration, and chlorination) from 2-amino-4-chlorobenzoic acid (I). The target compound has been for the first time fully characterized by melting point, mass-spectrometry, FT-IR, 1H-NMR and 13C-NMR spectroscopies.
Mesna is in a class of drugs known as chemoprotectants. Mesna is used for the prevention of urothelial toxicity in patients being treated with the antineoplastics ifosfamide or cyclophosphamide. In this study, a new method for synthesis of mesna from 1,2-dichloroethane using trithiocarbonate salt intermediate was continuously developed by the scale of 100g per batch. The synthesis was carried out in 3 steps: Firstly, sodium 2-chloroethanesulfonate was prepared from 1,2-dichloroethane by Strecker reaction. Secondly, sodium 2-chloroethanesulfonate was reacted with sodium trithiocarbonate, followed by acidification to pH 1.43 by H 2 SO 4 or HCl solution. Finally, mesna was obtained by adjusting pH to 6.6 with 1.5 M NaOH solution. The product was purified by crystallization from 96% ethanol. The overall yield of the synthesis process from 1,2-dichloroethane was 38.85 % based on sodium sulfite. The structures of the compounds were defined by IR, MS and NMR spectra data analysis. The product has met all quality requirements of British Pharmacopoeia 2015 therein the content of dried substance was 98.8%.
Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline sulfones have been used to build asymmetrical ether derivatives as inhibitors of signaling pathways governed by tyrosine kinases and the epidermal growth factor-receptor. In this paper, we report a facile synthesis of a novel quinazoline sulfone, 6-nitro-7-tosylquinazolin-4(3H)-one (III), using the modified protocol from 7-chloro-6-nitroquinazolin-4(3H)-one (I) and sodium p-toluenesulfinate (II). The structure of the title compound III was determined using mass-spectrometry, FT-IR, 1H-NMR, 13C-NMR, DEPT, HSQC (Heteronuclear single quantum coherence), HMBC (Heteronuclear Multiple Bond Correlation Spectroscopy) spectroscopies, and PXRD analysis.
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