Methylhydrazine → HCID 67214036, compound

Participants

Reaction Conditions

Reaction Steps

To a 1000 cm3 round bottom flask placed under an atmosphere of argon was added methylthioninium chloride (Medex™) (MTC.3H2O, MW 373.90, 50 g, 134 mmol) and acetonitrile (250 cm3). Methylhydrazine (MeNHNH2, MW 46.07, 14.26 cm3, 268 mmol) was added in portions. The mixture was heated to 35° 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, 101 cm3, 1.0 mol) and N,N-diisopropylethylamine (MW 129.24, 46.7 cm3, 268 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 then had water (250 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 (4×30 cm3), and dried in an oven at 60° C. for 3 hours to yield the title compound, which was purified from hot ethanol (120 cm3) by 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 were then dried in an oven at 60° C. for 3 hours (MW 327.45, 30.71 g, 93.8 mmol, yield 70%).

Provenance & Evidence