تفاعل #2122472

معادلة التفاعل

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

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product

المردود 61.3%

N,N-Dimethyl-N′-octyl Ethanimidamide

المردود 61.3%

المذيبات

toluene

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر