反応 #2122469

反応方程式

sodium hydroxide

dimethylcarbamyl chloride

Calcium carbonate

N-Hexyl acetamide

→

product

収率 38.8%

N,N-Dimethyl-N′-amyl ethanimidamide

収率 38.8%

溶媒

dichloromethane

toluene

反応条件

後処理

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

実験手順

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.

出典