Reaction #2122470

Reaction equation

N-hexyl acetamide

dimethylcarbamyl chloride

→

liquid

Yield 49.0%

N,N-Dimethyl-N′-hexyl Ethanimidamide

Yield 49.0%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe solution was refluxed under a nitrogen atmosphere for 24 h
2. 2
   OtherThe volatile materials were removed on a rotary evaporator
3. 3
   Otherat room temperature
4. 4
   workup.DISSOLUTIONThe residue was dissolved 30 mL of chloroform
5. 5
   workup.ADDITIONCalcium carbonate (4.2 g) was added
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITwas continued for another 30 min
8. 8
   OtherThe organic phase was separated
9. 9
   Extractionthe aqueous phase was extracted with dichloromethane (25 mL×3)
10. 10
    DryingThe combined organic phases were dried (calcium carbonate)
11. 11
    Otherthe solvent was removed on a rotary evaporator
12. 12
    workup.DISTILLATIONThe residue was distilled at 52-54° C./0.25 Torr (lit. bp 125° C./30 Torr (see Oszczapowicz, J.; Raczynska, E. J. Chem. Soc., Perkin Trans. 2 1984, 1643-1666)) product

Procedure

To a solution of N-hexyl acetamide (15.0 g, 105 mmol) in 15 mL of dry toluene was slowly added 11.2 g (104.9 mmol) of dimethylcarbamyl chloride. The solution was refluxed under a nitrogen atmosphere for 24 h. The volatile materials were removed on a rotary evaporator and then in vacuo at room temperature. The residue was dissolved 30 mL of chloroform and stirred vigorously with a solution of 4.2 g sodium hydroxide in 40 mL of water for 30 min. Calcium carbonate (4.2 g) was added and stirring was continued for another 30 min. The organic phase was separated and the aqueous phase was extracted with dichloromethane (25 mL×3). The combined organic phases were dried (calcium carbonate) and the solvent was removed on a rotary evaporator. The residue was distilled at 52-54° C./0.25 Torr (lit. bp 125° C./30 Torr (see Oszczapowicz, J.; Raczynska, E. J. Chem. Soc., Perkin Trans. 2 1984, 1643-1666)) product to yield 8.7 g (49%) of liquid (purity 99% by GC). IR (neat) 2955, 2926, 2856 (C—H), 1626 (N═C) cm−1. 1H NMR 3.18 (t, 2H, JHH 7.5 Hz, —CH2—N═), 2.87 (s, 6H, —N—(CH3)2); 1.87 (s, 3H, —N═C(CH3)—N); 1.49 (m, 2H, —CH2—CH2—N═); 1.25-1.4 (m, 6H, CH3—(CH2)3—); 0.88 (t, 3H, JHH 7.2 Hz, CH3). 13C NMR 158.79; 50.32; 38.07; 32.49; 32.00; 27.38; 22.80; 14.17; 12.45.

Source