Dimethylamine → N,N-Dimethyl-N′-octylmethanimidamide

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfate (34.7 g, 0.27 mole) was placed in a 300 ml 3-necked round bottom flask equipped with a heating mantle, magnetic stirrer, thermometer, addition funnel and calcium chloride drying tube. The reaction was stirred and warmed to 50° C. Heating was discontinued and dimethyl formamide (26 g, 0.36 mole) was added over a 10 minute period. The reaction temperature gradually rose to 85° C. The reaction was stirred an additional hour during which time the temperature fell to 45° C. The reaction was cooled and maintained between 0° and 10° C. while n-octylamine (32.3 g, 0.25 mole) in toluene (50 ml) was added over a period of 15 minutes. After the addition was complete, the addition funnel and drying tube were replaced by a dry ice/acetone condenser and gas inlet tube. The cooling bath was removed and gaseous dimethylamine (6.1 g, 0.14 mole) was added over a period of about 5 minutes. The reaction was stirred at room temperature for 1 hour. The reaction was extracted with sodium hydroxide (12.5 g, 0.31 mole) in water (50 ml), washed with brine (25 ml), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 44.5 g (97 %) of the title compound as a very light yellow liquid. GLC showed 99.6% of volatiles in a single peak.

Provenance & Evidence