Acid anhydride on reaction with primary amine gives compound having a functional group

If the compound were ethylamine, the IUPAC name would be ethanamine. The suffix "amine" tells you that the compound is an amine. In ethanamide, the suffix "amide" tells you that you have an amide group, that is, a C=O attached to an N atom. So "ethanamide" tells you that you have a two-carbon chain that includes a C=O attached to an N atom, i.e., CH3CONH2. The general rule for naming amides is that you replace the ending "oic acid" of the acid name with the ending "amide". So ethanoic acid becomes ethanamide. Don't forget that at the base of a carbonyl there is another carbon. Even though it looks like the double bond is just going to the oxygen, there is still a carbon there at the base of the double bond, which means that it would have three carbons on the left side of the molecule and therefore would be named as 'propan'. Hope this helps! Yes, the N atom is secondary. There are two different ways of classifying amides. One way is the primary, secondary, tertiary system. In a primary amide, the N atom is bound to one carbon – the carbonyl carbon. Successive substitutions of the amino H atoms by carbon atoms turn the amide into secondary and tertiary amides. The more common way is to describe amides as unsubstituted, monosubstituted, or disubstituted, according to the number of alkyl or aryl substituents on the N atom. Thus, N-methylpropanamide is a monosubstituted amide with a 2° N atom. What I want to do in this video is talk about a bunch of molecules or classes of mol...

Amines are a fundamentally important class of biologically active compounds and the ability to manipulate their physicochemical properties through the introduction of fluorine is of paramount importance in medicinal chemistry. Current synthesis methods for the construction of fluorinated amines rely on air and moisture sensitive reagents that require special handling or harsh reductants that limit functionality. Here we report practical, catalyst-free, reductive trifluoroethylation reactions of free amines exhibiting remarkable functional group tolerance. The reactions proceed in conventional glassware without rigorous exclusion of either moisture or oxygen, and use trifluoroacetic acid as a stable and inexpensive fluorine source. The new methods provide access to a wide range of medicinally relevant functionalized tertiary β-fluoroalkylamine cores, either through direct trifluoroethylation of secondary amines or via a three-component coupling of primary amines, aldehydes and trifluoroacetic acid. A reduction of in situ-generated silyl ester species is proposed to account for the reductive selectivity observed. The incorporation of fluorine into potential medicines can be used to modify conformation, basicity, intrinsic potency, membrane permeability and pharmacokinetic properties β-fluoroalkylamines are less basic than their hydrocarbon counterparts (p K aH 10.7 versus 5.7 for ethylamine and trifluoroethylamine respectively) 4 or borane reduction of trifluoromethylamides ...

Aromatic anhydrides may be synthesised by palladium-promoted carboxylation of arenes with carbon monoxide at 15 bar. Thus, benzoic anhydride was produced in 32% yield from benzene, whilst toluene and chlorobenzene resulted in regioisomeric mixtures of toluic acid anhydrides and chlorobenzoic acid anhydrides, respectively. Furan and thiophene were also converted to their respective three-substituted anhydrides ( Scheme 19) . Symmetrical aromatic anhydrides may be synthesised from aryl alkyl anhydrides by pyrolysis at 100–120°C under reduced pressure ( Scheme 20). Matsuda and co-workers have synthesised aryl alkyl anhydrides by palladium-catalysed insertion of carbon monoxide into diazonium tetra-fluoroborates in the presence of sodium acetate. This produces the mixed anhydrides in 65% to 83% yield, which can then be pyrolysed to give the symmetrical aromatic anhydrides. Similarly, direct synthesis of symmetrical aromatic anhydrides can be achieved . Anhydrides of chloroformic acid with both carboxylic and sulfonic acids have been reported. They are prepared at low temperatures, and are very reactive. Amino acids protected as their N-benzyloxycarbonyl derivatives form anhydrides on reaction with phosgene and triethylamine at −70°C . These anhydrides react with alcohols at −70°C to form esters. Reaction of unprotected amino acids with phosgene or bis(trichloromethyl) carbonate (triphosgene) without base at room temperature yields the cyclic amino acid carboxyanhydrides. Since...

How does an acid anhydride react with a primary amine? I thought it'll be some sort of condensation reaction, so I made the product by removing a water molecule and got a cyclic product. However, the product given is an open chain molecule (major). How does the reaction occur? How does the ring open? Could someone please give a detailed mechanism? P. S. What is the general reaction for primary amines and acid anhydrides? It should be very clear that a primary amine is a nucleophile and an acid anhydride an electrophile. In the series of carbonyl and carboxyl derivatives, an acid anhydride is classified as quite reactive: more so than aldehydes or ketones, much more than esters or amides but less than acid chlorides. Thus, we should all agree that the first step is the nucleophilic attack on the $\ce$ bond that wasn’t attacked) and a secondary amide. The secondary amide still has a lone pair we might consider to be nucleophilic — but that lone pair is taking part in amide resonance and is thus not available for nucleophilic attack (at least not well). And to remove the amide’s proton, we would need a strong base which we don't have. Thus, the amide side of the equation is far less reactive. What about the carboxylate? Thus highly symmetric structure is also very unreactive towards nucleophilic attack in the same way as an amide. Due to the negatively charged oxygen donating one of its lone pairs to the π system, the carbon atom is much less electrophilic than in an acid anh...

Reactions of amines Amines characteristically form +, adds to the 2SO 4, HNO 3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral 3N becomes R 3NR′ +X −. RNH 2+ R′X → RR′N +H 2X −→ RNH 2RR′NH + RN +H 3X − Although tertiary amines do not react with aldehydes and ketones, and secondary amines react only reversibly, primary amines react readily to form 2C=NR′. 3H, by removal of ―OH, such as RC(=O)―, RS(O) 2―, and so on). Reagents may be acid chlorides (RCOC1, RSO 2C1), 2O), or even Facts You Should Know: The Periodic Table Quiz The reaction with 2 (the acid chloride of 2CO 3), has major industrial importance. It can result in simple acylation to form 2+ COCl 2→ RN=C=O + 2HCl). Isocyanates are themselves acylating agents, of a type that also includes isothiocyanates (RN=C=S), 2C=C=O), and 2 −RNH 3 +). Reaction with 2), which functions as an acylating agent that is a source of the nitrosyl group (―NO), converts aliphatic primary amines to nitrogen and mixtures of alkenes and alcohols corresponding to the alkyl group in a complex process. R 2CH―CR 2―NH 2+ HNO 2→ R 2CH―CR 2NHNO → N 2 + R 2C=CR 2 or R 2CH―CR 2OH This reaction has been used for Van Slyke method. With aromatic primary amines, nitrogen is not lost if the reaction mixture is kept cool (usually 0 °C [32 °F]), and a 2 +X −, where Ar is an aryl group, is formed: ArNH 2 + HNO 2 + HX → ArN 2 +X − These highly reactive see Nitrous acid converts secondary amines (a...

\( \newcommand\) • • • Acid Anhydrides react with amines to form amides