3-methyl-1,3-thiazolidin-2-imine;hydroiodide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methoxide (2.16 g) was added to a mixture of 2-imino-3-methylthiazolidine hydroiodide (10.0 g) in ethanol (50 ml) and brought to reflux, with stirring. Phenylisothiocyanate (5.4 g) in ethanol (20 ml) was added to the mixture over 5 minutes and the resultant mixture heated under reflux, with stirring, for one hour then cooled in ice. Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol. to reflux under reflux with stirring, for one hour then cooled in ice Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethyl chloroformate (0.25 ml.) at -5° C. was added to a solution of 350 mg. of t-butoxycarbonylaminoacetic acid and 0.4 ml. of triethylamine in 10 ml. of methylene chloride at -5° C. After stirring 5 minutes at -5° C. there was added a solution of 610 mg. of 2-imino-3-methylthiazolidine hydrogen iodide and 1.0 ml. of triethylamine in 10 ml. of methylene chloride also at -5° C. Stirring was continued at -5° C. for 15 minutes and one hour at room temperature. The reaction mixture was washed with 40 ml. of 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried and concentrated to dryness. The residue was triturated with ether, petroleum ether and ether and finally collected to give pure N-(3-methylthiazolidin-2-ylidene)-t-butoxycarbonylaminoacetamide. at -5° C there was added a solution of 610 mg also at -5° C Stirring was continued at -5° C. for 15 minutes and one hour at room temperature The reaction mixture was washed with 40 ml of 20% (w/v) citric acid solution, sodium bicarbonate solution, and water, dried concentrated to dryness The residue was triturated with ether, petroleum ether and ether finally collected

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methoxide (2.16 g) was added to a mixture of 2-imino-3-methylthiazolidine hydroiodide (10.0 g) in ethanol (50 ml) and brought to reflux, with stirring. Phenylisothiocyanate (5.4 g) in ethanol (20 ml) was added to the mixture over 5 minutes and the resultant mixture heated under reflux, with stirring, for one hour then cooled in ice. Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol. to reflux under reflux with stirring, for one hour then cooled in ice Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium methoxide (2.16 g) was added to a mixture of 2-imino-3-methylthiazolidine hydroiodide (10.0 g) in ethanol (50 ml) and brought to reflux, with stirring. Phenylisothiocyanate (5.4 g) in ethanol (20 ml) was added to the mixture over 5 minutes and the resultant mixture heated under reflux, with stirring, for one hour then cooled in ice. Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol. to reflux under reflux with stirring, for one hour then cooled in ice Filteration gave analytically pure product, mpt 169°-170°, which may be recrystallised from isopropanol