Triclobisonium chloride

Chemical Name N,N,N, N -tetramethyl-N,N -bis[1-methy. 3-(2,2,6-trimethylcyclohexyl)-propyl] 1,6-hexanediaminium dichloride 

To a solution of 49 grams (0.25 mol) of cis-tetrahydroionone and 14,1 grams (0.12 mol) of 1,6-hexanediamine in 150 ml of ethanol was added 1 teaspoon of Raney nickel. The volume was adjusted to 300 ml with ethanol and the mixture was hydrogenated at 50°C and a pressure of 200 psi. The catalyst was filtered off, the filtrate was concentrated and the residual oil fractionated in vacuo to obtain N,N -bis[1-methyl-3-(2,2,6-trimethylcyclo-hexyOpropyl] -1,6-hexanediamine BP 192° to 202°C at 0.02 mm. 

To 217 grams (0.456 mol) of N,N -bis[1-methyl-3-(2,2,6-trimethylcyclohexyl)propyl]-1,6-hexanediamine were added 182 ml (3.04 mols) of formic acid (90%). The resulting colorless solution was cooled, then 91.3 ml (1.043 mols) of formaldehyde (37%) were added. The solution was heated at steam temperature with occasional shaking for 2 hours and then refluxed for 8 hours. The volatiles were distilled off at steam temperature under water vacuum and the residual oil was made strongly alkaline with 50% potassium hydroxide. 

The reaction product was extracted with ether. The ether extract was washed with water, dried and concentrated in vacuo. The residual oil was fractionated in vacuo to obtain N, N -bis [ 1-meth y I-3-( 2,2,6-trimethyl cyclohexyl) propyl] -N,N -dimethyl-1,6-hexanediamine, BPo,4 230° to 240°C, = 1.4833. An aliquot, when treated with an ethanolic hydrogen 

To 5 grams of N,N -bis(1-methyl-3-(2,2,6-trimethylcyclohexyl)propyl]-N,N -dimethyl-1,6-hexanediamine dissolved in 100 ml of methanol, at 4°C, were added 100 ml methanol containing 10 grams of methyl chloride. The solution was heated in a closed vessel at 60°C for 15 hours. The colorless solution was concentrated and the resulting white solid crystallized from ethanol-acetonitrile-ether to obtain N,N -bis[1-methyl-3-(2,2,6-trimethylcyclo-hexyDpropyl] -N,N -dimethyl-1,6-hexanediamine bis(methochloride) hemihydrate. 

Trade Name Manufacturer Cou ntry Year Introduced 

A mixture of 5.7 grams (0.02 mol) of 5-chloro-2,4-disulfamylaniline and 4.9 grams (0.04 mol) of dichloroacetaldehyde in 25 ml of dimethyl formamide was heated at the boiling temperature and under reflux for 30 minutes. The reaction mixture was thereafter poured into a mixture of ice and water to precipitate the desired 6-chloro-7-sulfamyl-3-dichloro-methyl-3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide as a crystalline solid melting at 250° to 270°C with decomposition. 

Patent 3,264,292 August 2, 1966 assigned to Abbott Laboratories 

Trade Name Manufacturer Country Year introduced 

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Fluoro uracil mercury Tegafur Formaldehyde Biperiden Bronopol Cortivazol Edetate disodium Glaziovine Hexetidine Meptazinol Metampicillin sodium Methylol riboflavin Nifurfoline Nifurtoinol Noxytiolin Oxymetazoline HCI Phenindamine tartrate Pipebuzone Thihexinol Timonacic sodium Triclobisonium chloride T romethamine Tyloxapol Formamide Cimetide Primidone Protriptyline Razo xane Spiperone Formic acid Bupivacaine... 

Triclobisonium chloride is hexamethylenebis [dimethyl[l-methyl-3-(2,2,6-trimethylcyclohexyl propyl] ammonium]dichloride. 

Triclobisonium chloride occurs as a white or nearly white, practically odorless, crystalline powder. 

The infrared spectrum of triclobisonium chloride is presented in Figure 1. The spectrum was measured with a Perkin-Elmer 621 Spectrophotometer on a KBr pellet containing 1.5 mg triclobisonium chloride/300 mg of KBr. 

The spectrum shown in Figure 2 was obtained on a Jeol 60 MHz NMR by dissolving 57.2 mg of triclobisonium chloride in 0.5 ml of CDCI3 containing tetramethylsilane as an internal reference (2). Due to the many nearly equivalent protons in this molecule, the NMR spectrum consists of broad bands in the 0 to 4 ppm region. The spectral assignments are given in Table I (2). 

Triclobisonium chloride exhibits no fluorescence when irradiated with white light. (3)... 

The mass spectrum of triclobisonium chloride shown in Figure 3 was obtained from a CEC 21-110 mass spectrometer with an ionizing energy of 70 eV (4). 

In this case the main product observed had a molecular weight of 504, C34H68N2 by high resolution analysis, which corresponds to triclobisonium chloride minus 2 CH Cl s. 

Triclobisonium chloride decomposes on melting. The decomposition range depends on the rate of heating. When the NF Class I procedure is used (5), triclobisonium chloride melts with decomposition between 243 and 253°C. 

The DSC scan for triclobisonium chloride, shown in Figure 4, was obtained using a Perkin-Elmer DSC-IB Calorimeter. The sample pan contained a small hole in the top to allow the decomposition products formed to escape. With a temperature program of 10°C/min., an endotherm was observed starting at 253,4°C which is due to the melt and/ or decomposition of the molecule (6). Due to the nature of this peak no AHf was calculated. 

The solubility data for triclobisonium chloride obtained at 25°C are given in Table II (7). 

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