反応 #302889

反応方程式

2,3-dimethylbenzylamine

2-chloroethylisocyanate

sodium hydroxide

→

title compound

収率 53.6%

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

収率 53.6%

溶媒

1,4-dioxane

ethyl acetate

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux where it
3. 3
   温度to cool
4. 4
   温度The reaction mixture was heated
5. 5
   温度to reflux for about 18 hours
6. 6
   濃縮The reaction mixture was concentrated under reduced pressure
7. 7
   その他to leave a viscous oil residue
8. 8
   洗浄washed with 20 mL of water
9. 9
   抽出The organic phase was extracted with 20 mL of 3.0 molar aqueous hydrochloric acid
10. 10
    抽出The aqueous extract
11. 11
    workup.ADDITIONby adding 3.0 molar aqueous sodium hydroxide
12. 12
    抽出the basic mixture was extracted with 50 mL of ethyl acetate
13. 13
    乾燥The extract was dried with sodium sulfate
14. 14
    ろ過filtered
15. 15
    濃縮the filtrate concentrated under reduced pressure

実験手順

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.

出典