반응 #2122469

반응 방정식

sodium hydroxide

dimethylcarbamyl chloride

Calcium carbonate

N-Hexyl acetamide

→

product

수율 38.8%

N,N-Dimethyl-N′-amyl ethanimidamide

수율 38.8%

용매

dichloromethane

toluene

반응 조건

후처리

1. 1
   온도refluxed under a nitrogen atmosphere for 16 h
2. 2
   기타The volatile materials were removed on a rotary evaporator
3. 3
   기타at room temperature
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGwas stirred another 30 min
6. 6
   기타The organic phase was separated
7. 7
   세척the aqueous phase was washed with dichloromethane (3×25 mL)
8. 8
   건조The combined organic liquids were dried (calcium carbonate)
9. 9
   기타the volatile materials were removed on a rotary evaporator
10. 10
    workup.DISTILLATIONThe residue was distilled at 40-41° C./0.25 Torr

실험 절차

N-Hexyl acetamide (10.0 g, 77.5 mmol) was added 10 mL of dry toluene, then 8.33 g (77.5 mmol) of dimethylcarbamyl chloride was slowly added and then refluxed under a nitrogen atmosphere for 16 h. The volatile materials were removed on a rotary evaporator and then in vacuo at room temperature. The residue was dissolved dichloromethane (30 mL) and 3.1 g (77.5 mmol) of sodium hydroxide dissolved aqueous solution (40 mL) was added. The mixture was stirred vigorously for 30 min. Calcium carbonate (3.1 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 liquids were dried (calcium carbonate) and the volatile materials were removed on a rotary evaporator. The residue was distilled at 40-41° C./0.25 Torr to yield 4.7 g (39%) of product (98.5% pure by GC). IR (neat) 2956, 2927, 2857 (C—H), 1626 (N═C) cm−1. 1H NMR 3.18 (t, 2H, JHH 7.5 Hz, —CH2—N═), 2.87 (s, 6H, —N—(CH3)2); 1.88 (s, 3H, —N═C(CH3)—N); 1.51 (m, 2H, —CH—CH2—N═); 1.25-1.4 (m, 4H, CH3—(CH2)2—); 0.90 (t, 3H, JHH 6.9 Hz, CH3). 13C NMR 158.90; 50.35; 38.15; 32.27; 29.98; 22.87; 14.31; 12.53.

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