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Dimethylformamide, DMF is an organic compound with the chemical formula H C O N(CH 3) 2.Its structure is HC(=O)−N(−CH 3) 2.Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids.
DMCC can also be formed in small amounts (up to 20 ppm) from dimethylformamide (DMF) in the Vilsmeier–Haack reaction [7] or when DMF is used as a catalyst in the reaction of carboxylic acids with thionyl chloride to the corresponding acyl chloride. [8] Synthesis of dimethylcarbamoyl chloride with dimethylformamide
The Vilsmeier reagent is an organic compound with the formula [(CH 3) 2 NCHCl]Cl. It is a salt consisting of the N,N-dimethyliminium cation ([(CH 3) 2 N=CHCl] +) and chloride anion. Depending on the particular reaction, the anion can vary. In typical POCl 3-based reactions, the anion is PO 2 Cl 2 −.
The first step of the Bouveault aldehyde synthesis is the formation of the Grignard reagent. Upon addition of a N , N -disubstituted formamide (such as dimethylformamide ) a hemiaminal is formed, which can easily be hydrolyzed into the desired aldehyde.
The chemical is a useful reagent for peptide synthesis reactions, where it activates the carboxylic acid partner for subsequent reaction with amines. It is commercially available as 50 % solution in DMF or ethyl acetate as a slightly yellow mixture.
HATU (Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium) is a reagent used in peptide coupling chemistry to generate an active ester from a carboxylic acid. HATU is used along with Hünig's base (N,N-diisopropylethylamine), or triethylamine to form amide bonds. Typically DMF is used as solvent, although other polar aprotic solvents can ...
The reaction of a substituted amide with phosphorus oxychloride gives a substituted chloroiminium ion (2), also called the Vilsmeier reagent. The initial product is an iminium ion (4b), which is hydrolyzed to the corresponding ketone or aldehyde during workup. [7] The Vilsmeier–Haack reaction
One reliable and rapid procedure is the Corey protocol in which the alcohol is reacted with a silyl chloride and imidazole at high concentration in DMF. [1] If DMF is replaced by dichloromethane, the reaction is somewhat slower, but the purification of the compound is simplified. A common hindered base for use with silyl triflates is 2,6 ...