Reaction #302889

Reaction equation

2,3-dimethylbenzylamine

2-chloroethylisocyanate

sodium hydroxide

→

title compound

Yield 53.6%

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

Yield 53.6%

Solvents

1,4-dioxane

ethyl acetate

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   Temperatureto reflux where it
3. 3
   Temperatureto cool
4. 4
   TemperatureThe reaction mixture was heated
5. 5
   Temperatureto reflux for about 18 hours
6. 6
   ConcentrationThe reaction mixture was concentrated under reduced pressure
7. 7
   Otherto leave a viscous oil residue
8. 8
   Washwashed with 20 mL of water
9. 9
   ExtractionThe organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid
10. 10
    ExtractionThe aqueous extract
11. 11
    workup.ADDITIONby adding 3.0 molar aqueous sodium hydroxide
12. 12
    Extractionthe basic mixture was extracted with 50 mL of ethyl acetate
13. 13
    DryingThe extract was dried with sodium sulfate
14. 14
    Filtrationfiltered
15. 15
    Concentrationthe filtrate concentrated under reduced pressure

Procedure

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.

Source