Dimethyl sulfate bromide

Etherification. The reaction of alkyl haUdes with sugar polyols in the presence of aqueous alkaline reagents generally results in partial etherification. Thus, a tetraaHyl ether is formed on reaction of D-mannitol with aHyl bromide in the presence of 20% sodium hydroxide at 75°C (124). Treatment of this partial ether with metallic sodium to form an alcoholate, followed by reaction with additional aHyl bromide, leads to hexaaHyl D-mannitol (125). Complete methylation of D-mannitol occurs, however, by the action of dimethyl sulfate and sodium hydroxide (126). A mixture of tetra- and pentabutyloxymethyl ethers of D-mannitol results from the action of butyl chloromethyl ether (127). Completely substituted trimethylsilyl derivatives of polyols, distillable in vacuo, are prepared by interaction with trim ethyl chi oro s il an e in the presence of pyridine (128). Hexavinylmannitol is obtained from D-mannitol and acetylene at 25.31 MPa (250 atm) and 160°C (129). 

All lation. In alkylation, the dialkyl sulfates react much faster than do the alkyl haHdes, because the monoalkyl sulfate anion (ROSO ) is more effective as a leaving group than a haHde ion. The high rate is most apparent with small primary alkyl groups, eg, methyl and ethyl. Some leaving groups, such as the fluorinated sulfonate anion, eg, the triflate anion, CF SO, react even faster in ester form (4). Against phenoxide anion, the reaction rate is methyl triflate [333-27-7] dimethyl sulfate methyl toluenesulfonate [23373-38-8] (5). Dialkyl sulfates, as compared to alkyl chlorides, lack chloride ions in their products chloride corrodes and requires the use of a gas instead of a Hquid. The lower sulfates are much less expensive than lower bromides or iodides, and they also alkylate quickly. 

Phenylacetonitrile Sec-Butyl bromide Thionyl chloride Dimethyl sulfate... 

Phenylacetonitrile is alkylated with secondary butyl bromide and the resultant nitrile is hydrolyzed to 3-methyl-2-phenylvaleric acid. The acid is converted to the acid chioride with thionyl chloride and the acid chloride is in turn reacted with 1-methyl-4-piperidinol. Finally dimethyl sulfate is reacted with the ester. 

Hydroxynicotinic acid Dimethyl sulfate 2-Thienyl bromide Methyl bromide... 

The reactions of 3-pyrazolylaminomethylenemalonate (1478, R = R1 = R2 = H) with dimethyl sulfate, ethyl iodide, or benzyl bromide in boiling THF in the presence of sodium hydride yielded -substituted AK3-pyrazolyl)aminomethylenemalonates (1478, R = R1 = H, R2 = Me, Et, PhCH2). 3-Pyrazolylaminomethylenemalonate (1478, R = COOfBu, R1 = R2 = H) was dimethylated with methyl iodide in DMF in the presence of sodium methylate at room temperature overnight to give /V-methyl-N-U -dimethyl-S-pyrazolyDaminomethylenemalonate (1478, R = COOfBu, R1 = R2 = Me) in 88% yield (85JHC729). 

Methanetrisulfonic acid, see Chloropicrin Methanol, see Acetic acid. Acetone. Acrylonitrile. Alachlor. 1-Butene, Dimethyl phthalate. Dimethyl sulfate. Formaldehyde. Methyl bromide. Methylene chloride. Methyl formate. Methyl methacrylate. Methyl mercaptan, 2-Methylpropene, Mevinphos, Nitromethane... 

Nitric acid, N-Methyl gluconamide. Acetic anhydride. Sodium bicarbonate. Methanol Dimethylurea, Nitric acid, Sulfuric acid. Methylene chloride, Sodium carbonate Anhydrous hydrazine, Cyanogen bromide, Isopropyl alcohol, Sodium nitrite, Sodium bicarbonate, Copper nitrate trihydrate, Nitric acid, Diethyl ether, Dimethyl sulfate... 

AA BAA CMC CPB CTAB DM SO IPC MVPQ PAA PDADMAB PEG PIPAA SDS SMA TEMED acrylamide methylene bisacrylamide critical micelle concentration cetylpyridinium bromide cetyltrimethylammonium bromide dimethylsulfoxide interpolymer complex methylvinylpiridine units quaternized by dimethyl sulfate poly(acrylamide) poly(diallyldimethylammonium bromide) polyethylene glycol) poly(isopropylacrylamide) sodium dodecyl sulfate sodium methacrylate tetramethylethylenediamine... 

The procedure given above is an adaptation of the methylation method first used by Sommelet and Ferrand3 and developed more fully by Clarke, Gillespie, and Weisshaus.2 /3-Phenylethyldi-methylamine has been prepared from /9-phenylethylamine by alkylation with dimethyl sulfate 4 by the reaction of fi-phenyl-ethylamine and of N-methyl- S-phenylethylamine with formaldehyde 6 by catalytic reduction of phenylacetonitrile in the presence of dimethylamine 3 by the reaction of dimethylamine with /3-phenylethyl chloride 7 8 9 and with /3-phenylethyl bromide 9 and by the reaction of phenylacetaldehyde with dimethylamine.10... 

Alkylation of chlorothiazide 154 (R = Cl) with dimethyl sulfate or with allyl bromide in aqueous or alcoholic alkali yields the 4-methyl and 4-allyl derivatives, respectively (60JOC970). Chlorothiazide-type compounds and their 3-oxo compounds, but not their 3,4-dihydro compounds, can be... 

Hexamethylene diamine Sodium hydroxide Dimethyl sulfate Hydrogen bromide... 

Sec-Butyl bromide Dimethyl sulfate Sodium hydroxide... 

From ethyl l-methylpiperidine-3-carboxylate (which was prepared by hydrogenation of ethyl nicotinate with Ni-catalyst and then by methylation by action dimethyl sulfate) and 2-thienyl magnesium bromide was synthesized l,l-di(thiophen-2-yl)-2-(3 -N-methylpiperidine), 3-(di-2-thienylmethylene)-l-methylpiperidine was obtained by dehydration of l,l-di(thiophen-2-yl)-2-(3 -N-methylpiperidine) by action of base. 

As has already been pointed out, the Finkelstein reaction can be conducted in situ in the absence of solvents. For example, alkylations of purine and pyrimidine bases with alkyl halides and dimethyl sulfate have been carried out by solid/liquid phase-transfer catalysis in the absence of any additional solvent [48], as have cyanation of haloalkanes [49] and / -eliminations [50]. Noteworthy is the synthesis of glycosyl isothiocyanates by the reaction of potassium thiocyanate with molten glycosyl bromide at 190 °C [51]. 

The synthesis of oxazolotropones 114d or 24a from bromotropone derivatives and dimethyl sulfate (Sections II,A,3,e and II,A,3,g, respectively) is explained by the reactivity of intermediate bromoxazolotropylium ion with methanol indeed, methyl bromide was detected in this reaction (Scheme 162 67CPB619). 

Tellurolates can be easily alkylated and, under suitable conditions, arylated to produce symmetrical and unsymmetrical diorgano tellurium (p. 387) and alkyl aryl tellurium (p.409) compounds. Examples of alkylating agents are primary ra-alkyl bromides and iodides, secondary alkyl bromides, dimethyl sulfate, allyl bromides6-9, chlorodifluoro-methane10, dichloroiodomethane11, methyl co-bromoalkanoates12, n, 3-halopropanoic... 

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