3-Carboalkoxy (or phenoxy) and 3-thiocarbo-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo(3.3.1)nonane and preparation

#This invention concerns novel 3-carboalkoxy (or phenoxy) and 3-thiocarboalkoxy (or phenoxy) derivatives of 7-cis-(3-chloro-2-propenyl)-1,3,5,7-tetraazabicyclo(3.3.1)nonane corresponding to the formula ##STR2## wherein X represents O or S and R represents C.sub.1-4 alkyl, phenyl or (C.sub.1-4)alkylphenyl. The compounds are viscous oils, readily soluble in organic solvents.

#The compounds are prepared in a 2-step process wherein cis-1-(3-chloro-2-propenyl)-3,5,7-triaza-1-azoniatricyclo(3.3.1.1.sup.3,7) decane chloride, commercially available as Dowicil.sup.(R) 200 antimicrobial, is treated with excess aqueous sodium hydroxide to give the ring-opened intermediate, hereinafter "basic oil", as follows:

#Dowicil 200 + NaOH.fwdarw.basic oil

#The following examples and teachings additionally describe specific embodiments and the best mode contemplated by the inventors of carrying out the invention.

#A quantity of 80 g (2.0 mole) of NaOH was dissolved in 500 ml water and cooled to room temperature. 100 Grams (0.4 mole) of Dowicil.sup.(R) 200 antimicrobial was added slowly to the caustic solution and the reaction mixture stirred ca. 15 minutes at ambient temperature. Extraction with benzene, drying over Na.sub.2 SO.sub.4 and evaporation of the benzene gave 72 g (78% yield) of the basic oil, described above, as a viscous oil.

#10.0 Grams (0.043 mol) basic oil intermediate was dissolved in 50 ml dry ether and filtered through Celite.sup.(R). 4.35 Grams (0.043 mol) freshly distilled triethylamine (phenyl isocyanate was added to the distillation flask to remove primary and secondary amines) was dissolved in 50 ml dry ether and added to the basic oil solution. The mixture was cooled to 0.degree. C. 3.87 Grams (0.043 mol) methyl chloroformate was dissolved in 25 ml dry ether and added slowly to the cold basic oil-triethylamine solution while stirring. A white precipitated formed immediately and the reaction was complete in 30 minutes. The precipitate was identified (NMR) as triethylamine-hydrogen chloride and was removed from the reaction mixture by filtration. The filtrate was evaporated on a rotary evaporator to give 7.85 g (70.2% yield) of a viscous oil identified (NMR) as the methyl carbamate derivative having the structure given above (X = O, R = CH.sub.3). Elemental analysis is consistent with the given structure.