Réaction #346627

Équation de réaction

n-butyl isocyanate

1-bromododecane

2-dimethylaminoethanol

ether

ether

→

2-hydroxyethyldimethyldodecylammonium bromide

N-butylcarbamate

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONdistilled in vacuum
2. 2
   AutreThe product, 2-dimethylaminoethyl N-butylcarbamate was collected at 106°/1.2 Torr
3. 3
   Autre(0.40 mole) of the above prepared amine
4. 4
   workup.WAITto stand stoppered for 9 days
5. 5
   Autreof product was obtained in crystalline form
6. 6
   AutreAfter two more recrystallizations from ethyl acetate
7. 7
   Autreat 115° C.

Mode opératoire

2-hydroxyethyldimethyldodecylammonium bromide, N-butylcarbamate is prepared in the following manner: A solution of 58 g. (0.65 mole) 2-dimethylaminoethanol in 150 ml. ether was treated over a period of 1.5 hours with 70 g. (0.71 mole) n-butyl isocyanate. After stirring another two hours the reaction mixture was stripped of ether and distilled in vacuum. The product, 2-dimethylaminoethyl N-butylcarbamate was collected at 106°/1.2 Torr. For quaternization 75 g. (0.40 mole) of the above prepared amine was combined with 105 g (0.42 mole) 1-bromododecane and allowed to stand stoppered for 9 days. At this time the reaction mixture was a stiff gel with some crystalline portions. By solution in ethyl acetate (900 ml.) and chilling, 160 g. of product was obtained in crystalline form. After two more recrystallizations from ethyl acetate, the material melted at 64° C. to liquid crystals and to a liquid at 115° C.

Source