Dimethylaniline reaction with

Dimethylaniline, reaction with silicon tetraisothiocyanate to yield... 

On acetylation it gives acetanilide. Nitrated with some decomposition to a mixture of 2-and 4-nitroanilines. It is basic and gives water-soluble salts with mineral acids. Heating aniline sulphate at 190 C gives sulphanilic add. When heated with alkyl chlorides or aliphatic alcohols mono- and di-alkyl derivatives are obtained, e.g. dimethylaniline. Treatment with trichloroethylene gives phenylglycine. With glycerol and sulphuric acid (Skraup s reaction) quinoline is obtained, while quinaldine can be prepared by the reaction between aniline, paraldehyde and hydrochloric acid. 

The Li compound 588 formed by the ort/io-lithiation of A. A -dimethylaniline reacts with vinyl bromide to give the styrene derivative 589(433]. The 2-phe-nylindole 591 is formed by the coupling of l-methyl-2-indolylmagnesium formed in situ from the indolyllithium 590 and MgBr2, with iodobenzene using dppb[434]. 2-Furyl- and 2-thienyllithium in the presence of MgBr2 react with alkenyl halides[435]. The arylallenes 592 and 1,2,4-alkatrienes are prepared by the coupling reaction of the allenyllithium with aryl or alkenyl halides[436]. 

A very interesting approach to optically active sulphoxides, based on a kinetic resolution in a Pummerer-type reaction with optically active a-phenylbutyric acid chloride 269 in the presence of A,N-dimethylaniline, was reported by luge and Kagan (equation 149). In contrast to the asymmetric reductions discussed above, this procedure afforded the recovered sulphoxides in optical yields up to 70%. Chiral a, -unsaturated sulphoxides 270 were prepared via a kinetic resolution elaborated by Marchese and coworkers. They found that elimination of HX from racemic -halogenosulphoxides 271 in the presence of chiral tertiary amines takes place in an asymmetric way leading to both sulphoxides 270 and 271, which are optically active (optical yields up to 20%) with opposite configurations at sulphur (equation 150). 

Although diselenonium-, ditelluronium- and mixed sulfonium-selenonium dications can exhibit either oxidative or electrophilic properties in reactions with nucleophiles, substitution at the onium chalcogen atom is more typical.96 Owing to the increased stability of heavier dichalcogenium-dications, they react only with highly activated substrates such as aniline and tV,A-dimethylaniline, while no reaction is observed with phenol and diphenylamine.113 Reactions of ditelluronium dications with activated aromatics are also not known (Scheme 44).114... 

Recently, Juge and Kagan (68) reported that a more efficient kinetic resolution of racemic sulfoxides takes place in the Pummerer-type reaction with optically active a-phenylbutyric acid chloride 38 in the presence of N,A-dimethylaniline. In contrast to the asym-... 

Silicon tetraisothiocyanate, reaction with 2,6-dimethylaniline to yield 2,6-diraethylphenyl thiourea, 46, 70 Silver cyanide, reaction with alkyl halides in synthesis of isocyanides, 46, 77... 

The immonium ion derived from oxidation of N,N-dimethylaniline can be trapped by reaction with methanol to give the relatively stable a-methoxymethyl... 

Lidocaine Lidocaine, 2-(diethylamino)-A-(2,6-dimethylphenyl)acetamide (2.2.2), is synthesized from 2,6-dimethylaniline upon reaction with chloroacetic acid chloride, which gives a-chloro-2,6-dimethylacetanilide (2.1.1), and its subsequent reaction with diethy-lamine [11]. 

The second necessary fragment, 7-amino-3-(l-pyridinomethyl)cef-3-en-carbonic acid (32.1.2.80), is synthesized from cefalosporidin (32.1.2.79), a cephalosporin antibiotic that is used independently in medicine and which is synthesized in the form of an internal salt by reacting cefalotin (32.1.2.1) with pyridine to replace the acetoxyl group with a pyridine group. Initially treating cephaloridin with trimethylchlorosilane in the presence of dimethylaniline and then with phosphorous pentachloride, followed by a reaction with 1,... 

Chlorination of methyl 2,3(l >4//)-quinoxalinedion-5-ylcarboxylate was efficiently achieved by reaction with phosgene in DMF at room temperature in 90% yield <1999JHC1271>. Other procedures using phosphoryl chloride alone or with phosphoms pentachloride or A, A -dimethylaniline decrease remarkably the yields of dichloroquinoxaline. 

Alkylpyridines are aminated preferentially at the 2-position, but reaction is slower than in the parent system. Quinoline is difficult to aminate and only a low yield of 2-aminoquinoline (32%) is obtained from reaction with sodamide in toluene. When dimethylaniline is employed as solvent, 2-amino-3,4-dihydroquinoline (24%) becomes the major product, and the yield of 2-aminoquinoline drops to 7%. The best yields of 2-aminoquinoline (53-69%) have been obtained by using barium or potassium amide in liquid ammonia. Use of the potassium salt also produces a 10% yield of the 4-amino isomer. The... 

Oxadiazolinones, substituted, 391 Oxaziranes, oxidation of, 406 2-Oxazolidones, 442 Oximes, 395 oxidation of, 415, 416 reaction with C-nitroso compounds, 351 4,4 -[Oxybis(4-nitro-o-phenyleneazo)]bis-JV,N-(dimethylaniline), 294... 

Methyl benzoate, anisole, and diphenyl ether each give sandwich compounds with chromium vapor, although in rather low yield (32, 55, 110). Chromium appears to attack alkyl ethers and this deoxygenation probably competes with complexation with the aromatic oxygen compounds. No simple product has been isolated from chromium atoms and aniline, but bis(7V,7V-dimethylaniline)chromium has been prepared (32). The behavior of molybdenum and tungsten vapors closely resembles that of chromium in reactions with oxygen- and nitrogen-substituted arenes (113). 

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