Benzothiazolium iodide

The 7V-monomethylation of primary amines RNH2 (R = CsHn, Ci2H25, Ph, PhCH2CH2 etc.) has been accomplished in high yield by condensation with 3-methyl-2-(methylthio)benzothiazolium iodide, followed by treatment of the resulting imine with methyl iodide or methyl tosylate to give the salts 49. The latter yield the products RNHMe by the action of butylamine (equation 29)76. 

The reaction of benzothiazolium iodide (105) with 2 mol of a primary alii tic amine or 1 mol each of an aromatic amine and triethylamine gave benzothiazolimine (106). Methylation of (106) and subsequent treatment of the resulting amidinium salts (107) with butylamine afforded the corresponding fV-methyl-amine (Scheme 47). ... 

Bei der Umsetzung des 1,3-Benzotbiazols la mit Methyliodid werden die Amino- und die Hydroxy-Gruppe in die Reaktion eiubezogen man erhalt als Hauptprodukt 6-Benzyloxy-2-dimethylamino-5-methoxy-3-me-thyl-l,3-benzothiazolium-iodid (II 32,5% Schmp. 202-204 ) und daneben 12% 6-Benzyloxy-5-methoxy-i-methyl-2-methylamino-l,3-benzothiazolium-iodid (III Schmp. 224- 226° Zers.), 6,5% 6-BenzyIoxy-2-[(6-benzyloxy-5-methoxy-3-methyl-2,3-dihydro-l, 3-benzothiazol-2-yliden)-amino]-5-methoxy-3-methyl-l,3-ben-zothiazolium-iodid (IV Schmp. 265-267°) sowie 11% 6-Benzyloxy-2,5-dimethoxy-l,3-benzothiazol (V Schmp. 167-1690)360 ... 

Die Reaktion von 3-Methyl- bzw. 2,3-Dimethyl-l,3-benzothiazolium-iodid mit Natrium-cyanoboranat fiihrt zu den entsprechenden 2,3-Dihydro-l,3-benzothiazolen und Cyan-(2-dial-kylamino-phenylthio)-boranen, die jedoch in der Saure- und Basen-stabilen cyclischen Form vorliegen 2-Cyan-3,3-dialkyl-2,3-dihydro-[Pg.1034]

Squaric acid diesters react with 2- or 4-substituted pyridinium, quino-linium, and benzothiazolium iodides to yield 1,2-disubstituted dyes [16] (Structure 1). 1,2-Disubstituted dyes were also synthesized using Friedel-Crafts reaction of squaraine dichloride with various nucleophiles as a key step [27]. 

N-[4-(3-ethyl-2-benzothiazolylidene)-2- M butenylidene]piperidinium iodide 3-ethyl-2-(4-piperidino-1,3-butadien-yl)benzothiazolium iodide 483 5.2 B141 8293... 

Additives used in final products Fillers aluminum hydroxide, calcium carbonate, clay, carbon nanotubes, magnesium hydroxide, montmorillonite, red phosphorus, quartz, silica, wood fiber, zinc oxide, zinc powder Plasticizers EVAC is used as plasticizer in PVC and PLA therefore it seldom requires plasticization Antistatics 2-methyl-3-propyl benzothiazolium iodide, alkylether triethyl ammonium sulfate, organic amide Antiblocking tty amide, laponite, silica Release methylstyryl silicone oil Slip eru-camide, oleamide, stearamide Thermal stabilizer BHT ... 

In 1935 Evans and Smiles obtained 2-methyl-N-(2-nitrophenyl)benzothiazolium iodide (64) when 2-[N-acetyl-N-(2-nitrophenylamino)]benzenethiol (63) was treated with hydroiodic acid in acetone (scheme-18). The same salt was also isolated when 2-[N-acetyl-N-(2-nitrophenylamino)]benzenesulfinic add was reduced with hydriodic and sulfurous adds. The corresponding perchlorate was prepared by treating the benzenethiol with perchloric acid (Evans Smiles 1935). 

Due to the unavailability of data about the liquid range of the above benzothiazolium salts, it is not certain whether the salts should be classified as ionic liquids or not. Recently our group have prepared a series of benzothiazolium iodides in absence of any solvent, studied their physical properties and performed metathesis reactions. The benzothiazolium bistriflimides showed a good liquidity range near ambient temperatures and have wide... 

Decomposition temperatures of benzothiazolium iodide salts were determined by TGA, heating at 10 °C min-i under dried air atmosphere and are reported (table-2) as (i) onset to 5 wt% mass loss (Ts%dec) and (ii) onset to total mass loss (Tdec) (in parentheses). 

A soln. of 3-(2,6-dichlorophenyl)-l-(benzothiazol-2-ylmethyl)-l-(2-hydroxyethyl)-thiourea in dry methanol containing 7 moles methyl iodide refluxed 20 hrs. under Ng 2-(2-hydroxyethyl)-l-methylthioimidazo[5,l-b]benzothiazolium iodide. Y 51%. J. Ashby and D. Griffiths, Synthesis 1975, 511. 

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