반응 #2122471

반응 방정식

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

→

product

수율 53.0%

N,N-Dimethyl-N′-heptyl Ethanimidamide

수율 53.0%

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 in vacuo
3. 3
   workup.DISSOLUTIONThe residue, dissolved 30 mL of dichloromethane
4. 4
   기타The organic phase was separated
5. 5
   추출the aqueous phase was extracted with dichloromethane (30 mL×3)
6. 6
   건조The combined organic phases were dried (calcium carbonate)
7. 7
   기타the solvent was removed on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled at 63-64° C./0.25 Torr

실험 절차

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).

출처