Réaction #2122472

Équation de réaction

Calcium carbonate

Dimethylcarbamyl chloride

N-octyl acetamide

sodium hydroxide

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product

Rendement 61.3%

N,N-Dimethyl-N′-octyl Ethanimidamide

Rendement 61.3%

Solvants

toluene

water

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source