Acetone dimethylamino

A A Dimethylamino)phenol. 3-Hydroxy-A7,A7-dimethylariiline (14) forms white needles and is soluble in alkaU, mineral acid, ethanol, diethyl ether, acetone, and benzene and practically insoluble in water. 

First, dimethylamino-2-phenoxyethane was made by reacting chloro-2-phenoxyethane with dimethylamine. Benzyl chloride (10 grams) was then added to a solution of 1-dimethylamino-2-phenoxyethane (12.3 grams) in acetone (35 ml). The mixture warmed spontaneously and N-benzyl-N,N-dimethyl-N-2-phenoxyethylammonium chloride slowly crystallized. After 24 hours, this solid was filtered off, washed with fresh acetone and dried immediately in vacuo, MP 135°-136°C. 

Another redox reaction leading to arenediazonium salts was described by Morkov-nik et al. (1988). They showed that the perchlorates of the cation-radicals of 4-A,A-dimethylamino- and 4-morpholinoaniline (2.63) react with gaseous nitric oxide in acetone in a closed vessel. The characteristic red coloration of these cation-radical salts (Michaelis and Granick, 1943) disappears within 20 min., and after addition of ether the diazonium perchlorate is obtained in 84% and 92% yields, respectively. This reaction (Scheme 2-39) is important in the context of the mechanism of diazotization by the classical method (see Sec. 3.1). 

Alternatively make up a stock solution of 10 g 4-(dimethylamino)-benzaldehyde in concentrated hydrochloric acid and dilute one part by volume with 4 to 10 parts by volume acetone inunediately before spraying [20. 25, 26, 28, 29, 44],... 

Improved selective acylation of 4,6 4, 6 -di-0-benzylidene-a,a-trehalose was achieved in acetone by the following method, in which a gentle liberation of -acyl-imidazole occurs on the conversion of benzotriazolyl-iV-oxytris(dimethylamino)phos-phonium hexafluorophosphate with the carboxylic acid in the presence of triethylamine and addition of imidazole 1199 ... 

Dissolve 6 mmol of 4-(dimethylamino)pyridine in 10 ml of dry acetone (base). 

Convert indole to indolyl-3-methyl-ketone (I) by treating indolyl-Mg-Br (preparation already described) with acetyl-Cl, by treating indole in POCl3 with dimethylacetamide (Vilsmeier reaction), or by reacting indole with diketene (ACS 22,1064(1968)). 15.9 g (1) in 50 ml methanol cool, stir and add dropwise 16 g Br2. Reflux 1 Vi hours on water bath cool, filter, wash with ether and recrystallize-methanol to get 18 g indolyl-3-Br-methyl-ketone (II). Dissolve 11.9 g (II) in 60 ml warm isopropanol and add 11 g 3 8% aqueous DMA (or equimoiar amount other amine) reflux one hour on water bath. Filter (recrystallize-ethanol) to get 8.5 g indolyl-3-dimethylamino-methyl ketone (III). Add 4.6 g (0.02 M) (III) in 30 ml tetrahydrofuran to 2.3 g lithium aluminum hydride in 50 ml tetrahydrofuran, stir one-half hour at room temperature and reflux two hours. Add a little water dropwise and extract the precipitate with acetone. Dry, evaporate in vacuum the combined organic phases to get an oil which will precipitate with ether-petroleum ether to give DMT. (Ill) should be tested for psychedelic activity. Dialkyltryptamines BCSJ 11,221 (1936), BSC 2291 (1966)... 

The reaction mixture of dimethyl AUV-dimethylaminothiocarbonyl-malonate and dimethyl sulfate in the presence of potassium carbonate in acetone was boiled for 6 hr to give methylthio(dimethylamino)methy-lenemalonate (337) in 60% yield (69T4649). 

Amino-1 -p-chlorophenyl-4-dimethylamino-1,2-dihydro-2,2-dimethyl-s-triazine (CXXXVII) was obtained from acetone and 1-p-chlorophenyl-5,5-dimethylbiguanide under acid conditions, and was isomerised by alkali to 6-p-chloroanilino-4-dimethylamino-l,2-dihydro-2,2-dimethyl-s-triazine (CXXXVIII), which also arose directly under basic conditions (95). Piperidine was found useful in promoting an analogous condensation (534). 

An interesting case of the addition of ketone hydrazone is observed in the reaction of acetone dimethylhydrazone with DMAD, wherein the initial nucleophilic attack is through the imino nitrogen, leading to products such as dimethyl A-isopropylidine-lV-dimethylamino-2-aminomaleate (132) and the dihydropyridine derivative (133). A small amount of the dimethylhydrazone of oxaloacetic ester (134) has also been observed in this reaction (Scheme 20). ... 

A couplingreagent 1.4 mg DABITC (4-(dimethylamino)azoben-zene-4 -isothiocyanate, Mr 282.4, recrystallized from acetone) is dissolved in 1.0 ml acetone. The solution is divided into 40 pi aliquots, and acetone is evaporated by nitrogen. The aliquots are stable in a desiccator at room temperature for months. 

To prepare the Ehrlich reagent, solution I (10% 4-(dimethylamino)benzaldehyde in coned HC1) is first made. Just before use, solution I and acetone (1 4) are mixed in a fume hood and used as a spray. 

To 238 mmol of the rra 5-5-alkyl-2-tert-butyl-3-methyl-4-imidazolidinone 7 (R1 = CH3) are added 65.9 g (302 mmol) of di-terr-butyl dicarbonate and 2.8 g (22.9 mmol) of 4-(dimethylamino)pyridine in 400 mL of acetone with cooling. After 8 h at 20 °C, 32.4 mL (232 mmol) of triethylamine are added and, after 2 h of stirring, 20 mL of water is added and the mixture is stirred for a further 2 h. After evaporation of the acetone, the residue is extracted with diethyl ether and the organic phase is washed with two 100-mL... 

A dry 50 mL Schlenk reaction tube was flushed with nitrogen and charged with a mixture of 7 (527mg, l.Ommol), 1,3-dicyclohexylcarbodiimide (1.04g, 5mmol), pentafluorophenol (920 mg, 5 mmol), 4-(dimethylamino)pyridine as the catalyst and the aminomethylated polystyrene (930 mg, 1.07 mmol g ) in dry dichloromethane (20 mL). The mixture was stirred at room temperature for 24h under a N2 atmosphere. The polymer was filtrated, rinsed sequentially with CH2CI2 and acetone and dried at 50 °C in vacuo to yield the polymer-bound ligand 8 as pale yellow beads. 

The chloroform layer is distilled to dryness and the residue is dissolved in 1.5 1. of acetone under reflux. The hot acetone solution is filtered and then allowed to cool in a refrigerator. Yellow 4,4 -bis(dimethylamino)benzil crystallizes from the acetone solution. It is separated by filtration and washed with 100... 

Synthesis (Pohland, 1953 1955 1963 janssen and Karel (Janssen)1956 Sullivan et al., 1963) In the Grignard reaction of 3-dimethylamino-2-methyl-1-phenyl-propan-lone with benzylmagnesium chloride 4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol is formed. The preferred product is the a-diastereomer(75 % a-form, 15 % p-form). The a-form crystallizes and the diastereomeric p-form remains in solution, because of its better solubility. Racemic resolution to obtain the analgetically (+) enantiomer can be achieved on the pure a-Grignard product via fractional crystallization of the salts with D-camphorsulfonic acid. Alternatively the resolution can be achieved by treating the racemic mannich product 3-dimethylamino-2-methyl-1-phenyl-propan-1-one with (-)-dibenzoyltartaric acid in acetone as solvent. 

Graft copolymers of polyamides using pre-irradiation gamma-rays techniques have been reported for styrene (130), in solution, in the presence of water (40), in alcohols or acetone solution (131), vinyl acetate (130), methacrylic acid in water (132) or methanol solution (129), methyl (133) and ethyl (130) acrylates, 2-ethylhexyl acrylate (55,134), methyl methacrylate (130), in methanol solution (129), 2-dimethylamino ethyl methacrylate quaternary salts (135), acrylamide in aqueous medium (128,136), acrylonitrile (130,137), and 4-vinyl pyridine in aqueous solution (128). 

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