Methyl, alcohol ammonium iodide

N-Methylethylamine has been prepared by heating ethyl-amine with methyl iodide in alcohol at 100° 3 by the hydrolysis of N-methyl-N-ethylarenesulfonamides,4-5 -nitroso-N-methyl-N-ethylaniline,6 or methylethylbenzhydrylidene ammonium iodide 7 by catalytic hydrogenation of ethyl isocyanate or ethyl isocyanide 8 and by the reduction of ethyl isocyanate by lithium aluminum hydride,9 of N-methylacetisoaldoxime by sodium amalgam and acetic acid,10 or of a nitromethane/ethylmagnesium bromide adduct by zinc and hydrochloric acid.11... 

When diethyl (cyclic amino)methylenemalonates (274, n = 1,X = CH2, O, NMe) were reacted with methyl iodide in boiling isobutyl alcohol, quaternary ammonium iodides (1487) were obtained (64JMC68). 

Methylamine occurs in herring brine 2 in crude methyl alcohol from wood distillation,3 and in the products obtained by the dry distillation of beet molasses residues.4 It has been prepared synthetically by the action of alkali on methyl cyanate or iso-cyanurate 5 by the action of ammonia on methyl iodide,6 methyl chloride,7 methyl nitrate,8 or dimethyl sulfate 9 by the action of methyl alcohol on ammonium chloride,10 on the addition compound between zinc chloride and ammonia,11 or on phos-pham 12 by the action of bromine and alkali on acetamide 13 by the action of sodamide on methyl iodide 14 by the reduction of chloropicrin,15 of hydrocyanic or of ferrocyanic acid,16 of hexamethylenetetramine,17 of nitromethane,18 or of methyl nitrite 19 by the action of formaldehyde on ammonium chloride.20... 

It is reported that trimethylamine in combination occurs in large amounts in beet-root residues 2 and can be obtained from them by the action of caustic soda it occurs also in herring brine.3 From both of these sources, however, the substance is obtained in an impure state and can be purified only by rather tedious methods. This is indicated by the fact that trimethylamine has always been an expensive substance. Synthetic methods for its production are by the action of methyl iodide on ammonia 4 by the distillation of tetramethylammo-nium hydroxide 6 by the action of magnesium nitride upon methyl alcohol 6 by the action of zinc upon trimethyloxy-ammonium halides 7 by the action of formaldehyde upon ammonium chloride under pressure 8 by the action of ammonium chloride upon paraformaldehyde.9 Of these syn-... 

H. M. Dawson and J. McCrae, D. P. Konowaloff, and W. Gaus also used soln. of various salts of the alkali metals, and of potassium, sodium, cupric, or barium hydroxide in place of water and also copper sulphate, copper chloride, zinc sulphate, and cadmium iodide while M. 8. Sherrill and D. E. Russ examined the effect of ammonium chromate. W. Herz and A. Kurzer examined the distribution of ammonia between water and a mixture of amyl alcohol and chloroform. Observations on the distribution of ammonia between water and chloroform were made by T. S. Moore and T. F. Winmill, G. A. Abbott and W. C. Bray, and J. M. Bell. J. H. Hildebrand gave for the molar fraction N X104 of ammonia at 1 atm. press., and 25°, dissolved by ethyl alcohol, 2300 methyl alcohol, 2730 and water, 3300. 

A number of eases of satisfactory agreement with theoretical requirements have been found in methyl alcohol solutions this is particularly the case for the chlorides and thiocyanates of the alkali metals. Other electrolytes, such as nitrates, tetralkyl-ammonium salts and salts of higher valence types, however, exhibit appreciable deviations. These discrepancies become more marked the lower the dielectric constant of the medium, especially if the latter is noii-hydroxylic in character. The conductance of potassium iodide has been determined in a number of solvents at 25 and the experimental and calculated slopes of the plots of A against Vc arc quoted in Table XXV,... 

When it is not possible to employ potassium chloride solution, e.g., if one of the junction solutions contains a soluble silver, mercurous or thallous salt, satisfactory results can be obtained with a salt bridge containing a saturated solution of ammonium nitrate the use of solutions of sodium nitrate and of lithium acetate has also been suggested. For non-aqueous solutions, sodium iodide in methyl alcohol and potassium thiocyanate in ethyl alcohol have been employed. 

Salvarsan dihydrochloride (100 grams) in 800 c.c, of methyl alcohol and 300 c.c. of water containing -i gram-molecules of sodium hydroxide is treated with a solution of 50 grams of sodium chloroacetate and 86 grams of potassium iodide in 5 to 10 parts by weight of water. The mixture is heated at 60° to 65° C. in an inert atmosphere for two to three hours, then faintly acidified, when the glycine derivative is precipitated. The product is a yellow powder, readily soluble in alkali and excess of acid, but insoluble in all the usual solvents. The sodium salt is yellowish-brown and dissolves readily in water with neutral reaction. The potassium and ammonium salts are also kno vn. 

Hofmann exhaustive methylation The treatment of an amine with excess methyl iodide to form the quaternary ammonium iodide, which is then converted into the hydroxide by treatment with moist silver oxide on heating in an aqueous or alcoholic solution, it decomposes to give an alkene. Also called the Hofmann degradation. 

Id) To prepare the quaternary ammonium iodide, the amino-alcohol above was dissolved in a minimum amount of anhydrous ether and was treated with its own weight of methyl iodide. A well-crystallized product was obtained and was washed with anhydrous ether. (Melting point 189°C to 191°C). 

Orthoesters are converted into esters with TMS-I. The dimethyl acetal of formaldehyde, methylal, affords iodomethyl methyl ether in good yield (eq 12) 7a (in presence of alcohols, MOM ethers are formed). 7b a-Acyloxy ethers also furnish the iodo ethers, e.g. the protected 8-acetyl ribofuranoside gave the a-iodide which was used in the synthesis of various nucleosides in good yield (eq 13). Aminals are similarly converted into immonium salts, e.g. Eschenmoser s reagent, Dimethyl(methylene)ammonium Iodide, in good yield. ... 

Acetamide Alkyl trimethyl ammonium chloride Ammonium caprylate Benomyl Benzimidazole carbamate 1,2-Benzisothiazolin-3-one Benzyltriethyl ammonium chloride Chlorine dioxide p-Chloro-m-cresol Chlorophene Cocodiamine acetate Dialkyl methyl benzyl ammonium chloride DIchlorobenzyl alcohol DImethoxytetrahydrofuran DM DM hydantoin Glyoxal Hexachlorophene Hydrogenated tallowtrlmonlum methosulfate N,N -Methylene bismorphollne 2-Methyl-4,5-trlmethylene-4-lsothlazolln-3-one Quaternlum-18 methosulfate Thiophanate Tributyl phosphine Tributyl (tetradecyl) phosphonlum chloride Trioctyl (octadecyl) phosphonlum Iodide VInylene bisthlocyanate biocide mfg. 

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