Dimethylformamide → N,N-Dimethyl-N′-octylmethanimidamide

Participants

Reaction Conditions

Reaction Steps

Dimethyl sulfate (126.1 g, 1.0 mole) was heated to 65° C. The temperature was maintained at 60°-70° while dimethylformamide (73.1 g, 1.0 mole) was added over a period of about 30 minutes. After the addition was complete, the reaction was heated at 70° C. for 7 hours, then cooled to below 30° C. n-Octylamine (129.2 g, 1.0 mole) was added over a 20 minute period with external cooling to maintain the temperature at 40° C. The reaction was stirred an additional 3 hours at 40° C. after addition was complete. The reaction was cooled to about 10° C. and treated with toluene (200 ml), water (200 ml) and finally 27% sodium hydroxide solution (180 g 1.2 moles). The organic phase was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 190 g of a light yellow liquid which was fractionally distilled twice to yield 113 g (61%) of the title compound as a water white liquid. b.p. 115°-117° C. at 15 mm Hg.

Provenance & Evidence