Bromination is a type of electrophilic aromatic substitution reaction where one hydrogen atom of benzene or benzene derivative is replaced by bromine due to an electrophilic attack on the benzene ring. The purpose of this experiment is to undergo bromination reaction of acetanilide and aniline to form 4-bromoacetanilide and 2,4,6-tribromoaniline respectively. Since -NHCOCH3 of acetanilide and -NH2 of aniline are electron donating groups, they are ortho/para directors due to resonance stabilized structure. Even though the electron donating groups activate the benzene ring, their reactivities are different and result in the formation of different products during bromination. In acetanilide, the lone pair of the nitrogen is delocalized into the
2.2 Chemicals and reagents The API of AN (99.9% pure) 1000mg was purchased from market. HPLC grade acetonitrile (SD fine limited). Analytical grade hydrochloric acid ,sodium hydroxide flakes, hydrogen peroxide. Milli-Q Water purchased from market.. 2.3 Details of Method Chromatographic conditions: Reversed Phase High Performance liquid chromatography method with UV detection separation was achieved on zorbox Agilent Eclipsc XDB column c18(150 nm× 4.6 mm×5µm) as stationary phase with binary gradient mode solvent phase A. Composed of H3PO4(ortho phosphoric acid ) buffer ( pH ≈2, 0.02M) and phase B as Acetonitrile ,The Flow rate of the mobile phase was 1.0 mL/min and the total elution time including the column re-equilibration was approximately
d. Nirav Kapadia and others uses Oxa-pictet-spengler reaction as one of the key steps in the synthesis of new isochroman heterocycles containing a 4, 5, 6a,7-tetrahydrodibenzo[de,g]chromene and further performed the acidic cleavage of molecule to form phenanthrene alkaloids(33). e. Santosh J. Gharpure et al worked on stereoselective synthesis of oxazino[4,3-a]indoles via oxa-Pictet–Spengler reaction of indoles having N-tethered vinylogous carbonate(26). Furthur optimization of reaction conditions were done and explained in table 19& 20. Table 19. Scope of the Oxa-Pictet-Spengler reaction for the synthesis of oxazinoindoles ENTRY R1 R2 R3 PRODUCT YIELD DIASTERIOMER RATIO 1 H H Ph 69l 85 >19:1 2 H H CH2OBn 69a 60 >19:1 3 H ----------(CH2)4-----------
The IUPAC nomenclature for haloperidol is 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-1-(4-fluorophenyl)butan-1-one. Figure 1: 2-D structure of haloperidol (taken from https://pubchem.ncbi.nlm.nih.gov/compound/3559) Tacke et al (2008) analysed haloperidol in order to determine the physicochemical properties of the drug. At a pH of 7.4, it was discovered that haloperidol has a distribution coefficient (Log D) of
As mentioned in number 13, the data for the melting point makes sense because my pure product and given compound almost perfectly matched. 17. Again as explained in number 14, the TLC data made sense because my pure compound and 4-tert-butylbenzyl phenol had similar distances from the solvent origin of the plate. The presence of benzyl bromide and benzyl alcohol also explains how not all the product dissolved in the filtrate. The possible explanations and changes to make are similar to the previous questions.
3.3. Synthetic methodologies for dihydropyrimidinones 3.3.1. Classical method Scheme-1: The conventional method for the synthesis of DHPMs is the one-pot three-component reaction of benzaldehyde, ethyl acetoacetate and urea in the presence of an acid catalyst. The product of this novel one-pot, three components synthesis that precipitated on cooling of the reaction mixture was identified as 3,4-dihydropyrimidin-2(1H)-one and this reaction came to be known as “Biginelli reaction”, or “Biginelli condensation”, or “Biginelli dihydropyrimidine synthesis” after the name of its inventor “Pietro Biginelli”.1 Mechanism Forty years after Biginelli’s initial report, the first mechanism for the synthesis of DHPMs was conducted by Folkers and Johnson
The N‟-2- (bromophenyl)-N,N-dimethylurea 16 underwent lithiation on the nitrogen to form a monolithio intermediate using MeLi, followed by bromine-lithium exchange using t-BuLi to give the dilithio species 17. 14 The intermediate 17 was then exposed to carbon monoxide to give 18, which after cyclization forms the intermediate 19, followed by loss of LiNMe2 to give 20, and finally after work up with dilute acid yielded the isatin product 1. 1 13 14 15 6 N O O 1) MeLi, 0 C CO Br N H O NMe2 2) t-BuLi, 0 C Li N O NMe2 Li C N Li O Li O NMe2 N O NMe2 O Li Li -LiNMe2 N H O O Li H3O + X X X X X X A rather versatile and novel two step synthesis of isatins was presented by Mironov in 2001 and allowed for the preparation of isatins containing electron withdrawing groups such as - CF3, -NO2, and -Cl. The method is based on the reaction between aromatic isocyanides and tertiary amines,15 where in the first step, 2-triethylammonio-3-arylaminoindolates 23 were obtained from the corresponding aromatic formamides 21 without isolation of the intermediate isocyanides 22. 16 Heating the 2-triethylammonio-3-arylaminoindolates 23 in excess thionyl chloride followed by hydrolysis led to the target
Drapex 6.8, supplied by Galata Chemicals from Louisiana, was the ESO used. Boron triﬂuoride diethyl etherate, dimethyl benzyl amine, hexanoic anhydride (97%), n-hexanoic acid (99%) and n-octanoic acid (99%) were obtained from Sigma-Aldrich, USA, while sodium chloride and sodium bicarbonate were obtained from Fisher Scientiﬁc, USA and used as received. The AMC-2 catalyst was purchased from Aerojet Chemicals, California, US. Epon 828 (epoxy equivalent weight, EEW 185-192 g/eq. Hexion technical data sheet of Epon 828 issued September 2005) and Epon 1001F (EEW 525-550 g/eq.
5. Results and Discussions 5.1 Methyl erucate synthesis 5.1.1 Chemical analysis of erucic acid Physicochemical properties of erucic acid used for the synthesis of sucrose erucate were analyzed. The results of analysis are depicted in Table 5.1 Table 5.1 Analysis of erucic acid Acid value 166.03 ± 0.9 mg KOH/gm Iodine value 78.04 ± 1.2 g I2/100gm Saponification value 168.05 ± 0.8 mg KOH/gm 5.1.2 Analysis of methyl erucate After synthesis and purification of synthesized methyl erucate general characteristics of product were tested. The results obtained are shown in Table 5.2 and Figure 5.1 Figure 5.1 Color of methyl erucate Table 5.2 General characteristics of methyl erucate Color Light yellow Odour Consistency The results of chemical analysis
His theory based on structure and bonding and gave general explanation of bases and acids.. Due to the Lewis definitions of bases and acids it is possible for chemists to predict acid-base reactions. Acoordinate covalent bond is produced by the reaction of a Lewis acid and a Lewis base. According to this theory: • Acid-any species which is capable of receiving a pair of electrons • Base-any species which is capable of donating a pair of electrons (Oxford University Press, 2016) Ammonia also known as “alkaline air” was discovered in gaseous form by Joseph Priestley in 1774.