Acetonitrile → HCID 67214036, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 cm3 round bottom flask placed under an atmosphere of argon was added methylthioninium chloride (Medex™) (MTC.3H2O, MW 373.90, 10 g, 26.7 mmol) and acetonitrile (50 cm3). Hydrazine hydrate (NH2NH2.H2O, MW 50.06, 2.85 cm3, 58.7 mmol) was added in portions. The mixture was heated to 65° C. and stirred for 20 minutes. The resulting brown suspension was cooled to 5° C. using an ice-water bath. Acetic anhydride ((H3CCO)2O, MW 102.09, 25 cm3, 267 mmol) and N,N-diisopropylethylamine (MW 129.24, 9.3 cm3, 53.6 mmol) were added, and the resulting solution was heated at 100° C. for 2 hours with stirring. The reaction mixture was cooled to 5° C. and had water (50 cm3) added while stirring to give a light green solid, which was filtered using a standard Buchner funnel apparatus with a water aspirator, washed with water (4×6 cm3), and dried in an oven at 60° C. for 3 hours to yield the title compound, which was purified from hot ethanol (27 cm3), cooling the solution to 5° C. using an ice-water bath so that a precipitate formed, and filtering using a standard Buchner filter with a water aspirator in order to collect the crystals. The crystals where then dried in an oven at 60° C. for 3 hours (MW 327.45, 5.68 g, 17.4 mmol, yield 65%).

Provenance & Evidence