反应 #2122471

反应方程式

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

→

product

收率 53.0%

N,N-Dimethyl-N′-heptyl Ethanimidamide

收率 53.0%

溶剂

toluene

water

反应条件

后处理

1. 1
   温度the solution was refluxed under a nitrogen atmosphere for 16 h
2. 2
   其他The volatile materials were removed on a rotary evaporator in vacuo
3. 3
   workup.DISSOLUTIONThe residue, dissolved 30 mL of dichloromethane
4. 4
   其他The organic phase was separated
5. 5
   萃取the aqueous phase was extracted with dichloromethane (30 mL×3)
6. 6
   干燥The combined organic phases were dried (calcium carbonate)
7. 7
   其他the solvent was removed on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled at 63-64° C./0.25 Torr

实验过程

Dimethylcarbamyl chloride (6.86 g, 63.7 mmol) was added slowly to 10.0 g (63.7 mmol) of N-octyl acetamide in 10 mL of dry toluene and the solution was refluxed under a nitrogen atmosphere for 16 h. The volatile materials were removed on a rotary evaporator in vacuo. The residue, dissolved 30 mL of dichloromethane, was stirred vigorously with a solution of 2.55 g (63.7 mmol) of sodium hydroxide in 40 mL of water for 30 min. Calcium carbonate (2.55 g) was added to the mixture and stirring was continued for an additional 30 min. The organic phase was separated and the aqueous phase was extracted with dichloromethane (30 mL×3). The combined organic phases were dried (calcium carbonate) and the solvent was removed on a rotary evaporator. The residue was distilled at 63-64° C./0.25 Torr to yield 6.2 g (53%) of product (purity 99% by GC). IR 2956, 2925, 2854 (C—H), 1626 (N═C) cm−1. 1H NMR 3.17 (t, 2H, JHH 7.5 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, 10H, CH3—(CH2)5—); 0.88 (t, 3H, JHH 7.2 Hz, CH3).

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