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Schotten–Baumann Reaction
The Schotten–Baumann reaction is a method to synthesize amides from amines and acid chlorides: Schotten–Baumann reaction also refers to the conversion of acid chloride to esters. The reaction was first described in 1883 by German chemists Carl Schotten and Eugen Baumann. The name "Schotten–Baumann reaction conditions" often indicate the use of a two-phase solvent system, consisting of water and an organic solvent. The base in the water phase neutralizes the acid generated by the reaction while the starting materials and product remain in the organic phase, often dichloromethane or diethyl ether. Applications The Schotten–Baumann reaction or reaction conditions are widely used in organic chemistry. Examples: * synthesis of N-vanillyl nonanamide, also known as synthetic capsaicin * synthesis of benzamide from benzoyl chloride and a phenethylamine * synthesis of flutamide, a nonsteroidal antiandrogen * acylation of a benzylamine with acetyl chloride (acetic anhydride i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carl Schotten
Carl Schotten (12 July 1853 – 9 January 1910) was a German chemist who, together with Eugen Baumann, discovered the Schotten-Baumann reaction. The Schotten-Baumann reaction is a method to synthesize amides from amines and acid chlorides. Examples of this reaction include the synthesis of N-vanillyl nonanamide, also known as synthetic capsaicin. Life and work Schotten was born as the third child of a syndic at the University of Marburg, his mother was a daughter of a law professor. Although he lost his father at the age of two, his intellectual family background allowed him to receive a good education. After attending the gymnasium in Marburg and Schulpforta, he studied medicine at the University of Zurich. He later moved to the University of Leipzig and changed his subject to chemistry. Schotten joined the group of August Wilhelm von Hofmann at the University of Berlin in 1875. There, he received his Ph.D. in 1878 under the supervision of Ferdinand Tiemann. Schotten stayed thr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Flutamide
Flutamide, sold under the brand name Eulexin among others, is a nonsteroidal antiandrogen (NSAA) which is used primarily to treat prostate cancer. It is also used in the treatment of androgen-dependent conditions like acne, hirsutism, excessive hair growth, and hyperandrogenism, high androgen levels in women. It is taken oral administration, by mouth, usually three times per day. Side effects in men include breast tenderness and gynecomastia, enlargement, feminization (biology), feminization, sexual dysfunction, and hot flashes. Conversely, the medication has fewer side effects and is better-tolerated in women with the most common side effect being dry skin. Diarrhea and elevated liver enzymes can occur in both sexes. Rarely, flutamide can cause hepatotoxicity, liver damage, interstitial pneumonitis, lung disease, photosensitivity, sensitivity to light, methemoglobinemia, elevated methemoglobin, sulfhemoglobinemia, elevated sulfhemoglobin, and neutropenia, deficient neutrophils. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amide Synthesis Reactions
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent any group, typically organyl groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, as in asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amino group (); or, equivalently, an acyl (alkanoyl) group () joined to an amino group. Common amides are formamide (), acetamide (), benzamide (), and dimethylformamide (). Some uncommon examples of amides are ''N''-chloroacetamide () and chloroformamide (). Amides are qualified as primary, secondary, and tertiary according to the number of acyl groups bounded to the nitrogen atom. Nomenclature The core of amides is called the amide group (specifically, carboxamide group). In the ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lumière–Barbier Method
The Lumière–Barbier method is a method of acetylating aromatic amines in aqueous solutions. Illustrative is the acetylation of aniline. First aniline is dissolved in water using one equivalent of hydrochloric acid. This solution is subsequently treated, sequentially, with acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ... and aqueous sodium acetate. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion: Acetate then acts as a leaving group: The acetanilide product is insoluble in water and can therefore be filtered off as crystals. See also * Schotten–Baumann reaction References {{DEFAULTSORT:Lumiere-Barbier method Organic reactions Name reactions Amide synthesis reactions ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Peptide Synthesis
In organic chemistry, peptide synthesis is the production of peptides, compounds where multiple amino acids are linked via amide bonds, also known as peptide bonds. Peptides are chemically synthesized by the condensation reaction of the carboxyl group of one amino acid to the amine group, amino group of another. Protecting group strategies are usually necessary to prevent undesirable side reactions with the various amino acid side chains. Chemical peptide synthesis most commonly starts at the carboxyl end of the peptide (C-terminus), and proceeds toward the amino-terminus (N-terminus). Protein biosynthesis (long peptides) in living organisms occurs in the opposite direction. The chemical synthesis of peptides can be carried out using classical solution-phase techniques, although these have been replaced in most research and development settings by solid-phase methods (see below). Solution-phase synthesis retains its usefulness in large-scale production of peptides for industrial ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Peptide
Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides that have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty amino acids are called oligopeptides, and include dipeptides, tripeptides, and tetrapeptides. Peptides fall under the broad chemical classes of biological polymers and oligomers, alongside nucleic acids, oligosaccharides, polysaccharides, and others. Proteins consist of one or more polypeptides arranged in a biologically functional way, often bound to ligands such as coenzymes and cofactors, to another protein or other macromolecule such as DNA or RNA, or to complex macromolecular assemblies. Amino acids that have been incorporated into peptides are termed residues. A water molecule is released during formation of each amide bond.. All peptides except cyclic peptides have an N-terminal (amine group) and C-terminal (carboxyl g ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Amino Acid
Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 appear in the genetic code of life. Amino acids can be classified according to the locations of the core structural functional groups ( alpha- , beta- , gamma- amino acids, etc.); other categories relate to polarity, ionization, and side-chain group type ( aliphatic, acyclic, aromatic, polar, etc.). In the form of proteins, amino-acid '' residues'' form the second-largest component (water being the largest) of human muscles and other tissues. Beyond their role as residues in proteins, amino acids participate in a number of processes such as neurotransmitter transport and biosynthesis. It is thought that they played a key role in enabling life on Earth and its emergence. Amino acids are formally named by the IUPAC- IUBMB Joint Commi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Berichte Der Deutschen Chemischen Gesellschaft
''Chemische Berichte'' (usually abbreviated as ''Ber.'' or ''Chem. Ber.'') was a German-language scientific journal of all disciplines of chemistry founded in 1868. It was one of the oldest scientific journals in chemistry, until it merged with '' Recueil des Travaux Chimiques des Pays-Bas'' to form ''Chemische Berichte/Recueil'' in 1997. ''Chemische Berichte/Recueil'' was then merged with other European journals in 1998 to form '' European Journal of Inorganic Chemistry''. History Founded in 1868 as ''Berichte der Deutschen Chemischen Gesellschaft'' (, CODEN BDCGAS), it operated under this title until 1928 (Vol. 61). The journal was then split into: * ''Berichte der Deutschen Chemischen Gesellschaft, A: Vereins-Nachrichten'' (, CODEN BDCAAS), and * ''Berichte der Deutschen Chemischen Gesellschaft, B: Abhandlungen'' (, CODEN BDCBAD). Vol. 78 and 79 (1945–1946) were omitted and not published due to World War II. The journal was renamed ''Chemische Berichte'' (, CODEN CHBEAM) in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Emil Fischer
Hermann Emil Louis Fischer (; 9 October 1852 – 15 July 1919) was a German chemist and List of Nobel laureates in Chemistry, 1902 recipient of the Nobel Prize in Chemistry. He discovered the Fischer esterification. He also developed the Fischer projection, a symbolic way of drawing asymmetric carbon atoms. He also hypothesized lock and key mechanism of enzyme action. He never used his first given name, and was known throughout his life simply as Emil Fischer. Early years and career Fischer was born in Euskirchen, near Cologne, the son of Laurenz Fischer, a businessman, and his wife Julie Poensgen. After graduating he wished to study natural sciences, but his father compelled him to work in the family business until determining that his son was unsuitable. Fischer then attended the University of Bonn in 1871, but switched to the University of Strasbourg in 1872. He earned his doctorate in 1874 under Adolf von Baeyer with his study of phthaleins. Fischer remained with Baeyer i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetic Anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of cellulose acetate as well as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air. Structure and properties Acetic anhydride, like most organic acid anhydrides, is a flexible molecule with a nonplanar structure. The C=O and C-O distances are 1.19 and 1.39 Å. The Pi bond, pi system linkage through the central oxygen offers very weak resonance stabilization compared to the dipole, dipole-dipole repulsion between the two carbonyl oxygens. The energy barriers to bond rotation between each of the optimal aplanar conformations are quite low. Production Acetic anhydride was first synthesized in 1852 by the French chemist Charles Frédéric Gerhardt ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetyl Chloride
Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: : Laboratory routes Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (), phosphorus pentachloride (), sulfuryl chloride (), phosgene, or thionyl chloride (). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. Other methods When heated, a mixture of dichloroacetyl chloride and acetic aci ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
