反应 #2122468

反应方程式

Calcium carbonate

Dimethylcarbamyl chloride

N-hexyl acetamide

sodium hydroxide

→

product

收率 32.4%

N,N-Dimethyl-N′-butyl Ethanimidamide

收率 32.4%

溶剂

toluene

water

反应条件

后处理

1. 1
   温度After being refluxed under a nitrogen atmosphere for 16 h
2. 2
   其他the volatile materials were removed on a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 30 mL dichloromethane
4. 4
   其他The organic phase was separated
5. 5
   洗涤the aqueous phase was washed with dichloromethane (3×25 mL)
6. 6
   干燥The combined organic phases were dried over anhydrous calcium carbonate
7. 7
   其他The volatile materials were evaporated on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled, by 28-30° C./
9. 9
   其他0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37))

实验过程

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).

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