반응 #2122472

반응 방정식

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

→

product

수율 61.3%

N,N-Dimethyl-N′-octyl Ethanimidamide

수율 61.3%

용매

toluene

water

반응 조건

후처리

1. 1
   온도the solution was refluxed under a nitrogen atmosphere for 16 h
2. 2
   기타The volatile materials were removed on a rotary evaporator and in vacuo
3. 3
   workup.DISSOLUTIONThe residue, dissolved dichloromethane (30 mL)
4. 4
   기타The organic phase was separated
5. 5
   세척the aqueous phase was washed with dichloromethane (30 mL×3)
6. 6
   건조The combined organic phases were dried (calcium carbonate)
7. 7
   기타the volatile materials were removed on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled at 72-77° C./0.25 Torr

실험 절차

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).

출처