Reaction #2122468

Reaction equation

Calcium carbonate

Dimethylcarbamyl chloride

N-hexyl acetamide

sodium hydroxide

→

product

Yield 32.4%

N,N-Dimethyl-N′-butyl Ethanimidamide

Yield 32.4%

Solvents

toluene

water

Conditions

Workup

1. 1
   TemperatureAfter being refluxed under a nitrogen atmosphere for 16 h
2. 2
   Otherthe volatile materials were removed on a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 30 mL dichloromethane
4. 4
   OtherThe organic phase was separated
5. 5
   Washthe aqueous phase was washed with dichloromethane (3×25 mL)
6. 6
   DryingThe combined organic phases were dried over anhydrous calcium carbonate
7. 7
   OtherThe volatile materials were evaporated on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled, by 28-30° C./
9. 9
   Other0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37))

Procedure

Dimethylcarbamyl chloride (9.35 g, 86.9 mmol) was slowly added to a solution of N-hexyl acetamide (10.0 g, 86.9 mmol) in 10 mL of dry toluene. After being refluxed under a nitrogen atmosphere for 16 h, the volatile materials were removed on a rotary evaporator and then in vacuo for 2 h at room temperature. The residue was dissolved in 30 mL dichloromethane and the solution was stirred vigorously with a solution of 3.48 g (86.9 mmol) of sodium hydroxide in 40 mL water for 30 min. Calcium carbonate (3.48 g) was added to the mixture and it was stirred another 30 min. The organic phase was separated and the aqueous phase was washed with dichloromethane (3×25 mL). The combined organic phases were dried over anhydrous calcium carbonate. The volatile materials were evaporated on a rotary evaporator. The residue was distilled, by 28-30° C./0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37)), to yield 4.0 g (32%) of product, 98% pure (GC). IR (neat) 2956, 2929, 286 (C—H), 1629 (N═C) cm−1. 1H NMR 3.17 (t, 2H, JHH 7.2 Hz, —CH2—N═), 2.86 (s, 6H, —N—(CH3)2); 1.87 (s, 3H, —N═C(CH3)—N); 1.5 (m, 2H, —CH—CH2—N═); 1.25-1.4 (m, 6H, CH3—(CH)3—); 0.88 (t, 3H, JHH 7.2 Hz, CH3).

Source