Reaction #2122469

Reaction equation

sodium hydroxide

dimethylcarbamyl chloride

Calcium carbonate

N-Hexyl acetamide

→

product

Yield 38.8%

N,N-Dimethyl-N′-amyl ethanimidamide

Yield 38.8%

Solvents

dichloromethane

toluene

Conditions

Workup

1. 1
   Temperaturerefluxed under a nitrogen atmosphere for 16 h
2. 2
   OtherThe volatile materials were removed on a rotary evaporator
3. 3
   Otherat room temperature
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGwas stirred another 30 min
6. 6
   OtherThe organic phase was separated
7. 7
   Washthe aqueous phase was washed with dichloromethane (3×25 mL)
8. 8
   DryingThe combined organic liquids were dried (calcium carbonate)
9. 9
   Otherthe volatile materials were removed on a rotary evaporator
10. 10
    workup.DISTILLATIONThe residue was distilled at 40-41° C./0.25 Torr

Procedure

N-Hexyl acetamide (10.0 g, 77.5 mmol) was added 10 mL of dry toluene, then 8.33 g (77.5 mmol) of dimethylcarbamyl chloride was slowly added and then refluxed under a nitrogen atmosphere for 16 h. The volatile materials were removed on a rotary evaporator and then in vacuo at room temperature. The residue was dissolved dichloromethane (30 mL) and 3.1 g (77.5 mmol) of sodium hydroxide dissolved aqueous solution (40 mL) was added. The mixture was stirred vigorously for 30 min. Calcium carbonate (3.1 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 liquids were dried (calcium carbonate) and the volatile materials were removed on a rotary evaporator. The residue was distilled at 40-41° C./0.25 Torr to yield 4.7 g (39%) of product (98.5% pure by GC). IR (neat) 2956, 2927, 2857 (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); 1.88 (s, 3H, —N═C(CH3)—N); 1.51 (m, 2H, —CH—CH2—N═); 1.25-1.4 (m, 4H, CH3—(CH2)2—); 0.90 (t, 3H, JHH 6.9 Hz, CH3). 13C NMR 158.90; 50.35; 38.15; 32.27; 29.98; 22.87; 14.31; 12.53.

Source