Reacción #302889

Ecuación de reacción

2,3-dimethylbenzylamine

2-chloroethylisocyanate

sodium hydroxide

→

title compound

Rendimiento 53.6%

((2,3-dimethylphenyl)methyl)-1,3-oxazolin-2-ylamine

Rendimiento 53.6%

Disolventes

1,4-dioxane

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturato reflux where it
3. 3
   Temperaturato cool
4. 4
   TemperaturaThe reaction mixture was heated
5. 5
   Temperaturato reflux for about 18 hours
6. 6
   ConcentraciónThe reaction mixture was concentrated under reduced pressure
7. 7
   Otroto leave a viscous oil residue
8. 8
   Lavadowashed with 20 mL of water
9. 9
   ExtracciónThe organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid
10. 10
    ExtracciónThe aqueous extract
11. 11
    workup.ADDITIONby adding 3.0 molar aqueous sodium hydroxide
12. 12
    Extracciónthe basic mixture was extracted with 50 mL of ethyl acetate
13. 13
    SecadoThe extract was dried with sodium sulfate
14. 14
    Filtraciónfiltered
15. 15
    Concentraciónthe filtrate concentrated under reduced pressure

Procedimiento

A mixture of 1.0 gram (0.0074 mole) of 2,3-dimethylbenzylamine and 0.69 gram (0.0081 mole) of 2-chloroethylisocyanate in 10 mL of 1,4-dioxane was heated to reflux where it stirred for about 18 hours. The reaction mixture was allowed to cool and an aqueous solution of sodium hydroxide (4.0 mL of a 3.0 molar solution) was added. The reaction mixture was heated to reflux for about 18 hours then allowed to cool to ambient temperature. The reaction mixture was concentrated under reduced pressure to leave a viscous oil residue. The residue was suspended in 50 mL of ethyl acetate and washed with 20 mL of water. The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid. The aqueous extract was made basic by adding 3.0 molar aqueous sodium hydroxide and the basic mixture was extracted with 50 mL of ethyl acetate. The extract was dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield 0.81 gram of the title compound as an oil. The NMR spectrum was consistent with the proposed structure.

Fuente