반응 #2122468

반응 방정식

Calcium carbonate

Dimethylcarbamyl chloride

N-hexyl acetamide

sodium hydroxide

→

product

수율 32.4%

N,N-Dimethyl-N′-butyl Ethanimidamide

수율 32.4%

용매

toluene

water

반응 조건

후처리

1. 1
   온도After being refluxed under a nitrogen atmosphere for 16 h
2. 2
   기타the volatile materials were removed on a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 30 mL dichloromethane
4. 4
   기타The organic phase was separated
5. 5
   세척the aqueous phase was washed with dichloromethane (3×25 mL)
6. 6
   건조The combined organic phases were dried over anhydrous calcium carbonate
7. 7
   기타The volatile materials were evaporated on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled, by 28-30° C./
9. 9
   기타0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37))

실험 절차

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).

출처