反应 #2122472

反应方程式

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

→

product

收率 61.3%

N,N-Dimethyl-N′-octyl Ethanimidamide

收率 61.3%

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 and in vacuo
3. 3
   workup.DISSOLUTIONThe residue, dissolved dichloromethane (30 mL)
4. 4
   其他The organic phase was separated
5. 5
   洗涤the aqueous phase was washed with dichloromethane (30 mL×3)
6. 6
   干燥The combined organic phases were dried (calcium carbonate)
7. 7
   其他the volatile materials were removed on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled at 72-77° C./0.25 Torr

实验过程

Dimethylcarbamyl chloride (6.29 g, 58.4 mmol) was added slowly to 10.0 g (58.4 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 and in vacuo. The residue, dissolved dichloromethane (30 mL), was stirred strongly for 30 min with a solution of 2.34 g (58.4 mmol) of sodium hydroxide in 40 mL of water. Calcium carbonate (2.34 g) was added to the mixture and it was stirred an additional 30 min. The organic phase was separated and the aqueous phase was washed with dichloromethane (30 mL×3). The combined organic phases were dried (calcium carbonate) and the volatile materials were removed on a rotary evaporator. The residue was distilled at 72-77° C./0.25 Torr to yield 7.1 g (61%) of product (purity 99% by GC). IR (neat) 2955, 2924, 2853 (C—H), 1627 (N═C) cm−1. 1H NMR 3.17 (t, 2H, JHH 6.9 Hz, —CH2—N═), 2.86 (s, 6H, —N—(CH3)2); 1.87 (s, 3H, —N═C(CH3)—N); 1.5 (m, 2H, —CH2—CH2—N═); 1.25-1.4 (m, 10H, CH3—(CH2)5—); 0.88 (t, 3H, JHH 6.1 Hz, CH3).

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