反応 #549237

反応方程式

1-chloro-2-hydroxy-3-phenoxypropane

acetate

acetyl chloride

trichloroacetamidine

→

N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride

溶媒

tetrahydrofuran

acetic acid

tetrahydrofuran

反応条件

後処理

1. 1
   温度The mixture is heated
2. 2
   温度at reflux for 3 hours
3. 3
   濃縮concentrated to an oil, which
4. 4
   洗浄washed well with water
5. 5
   乾燥The benzene layer is dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   workup.ADDITIONtreated with excess ethanolic hydrogen chloride
8. 8
   その他to provide the crude hydroxy amidine hydrochloride
9. 9
   その他The reaction mixture is evaporated
10. 10
    workup.ADDITIONtreated with benzene
11. 11
    その他evaporated to dryness

実験手順

A solution of 9.3 g. (0.05 mole) of 1-chloro-2-hydroxy-3-phenoxypropane in 100 ml. of tetrahydrofuran is mixed with a solution of 8.1 g. (0.05 mole) of trichloroacetamidine, also in tetrahydrofuran. The mixture is heated at reflux for 3 hours, and concentrated to an oil, which is taken up in benzene and washed well with water. The benzene layer is dried over magnesium sulfate, filtered, and treated with excess ethanolic hydrogen chloride to provide the crude hydroxy amidine hydrochloride. This is dissolved in glacial acetic acid and converted to the acetate by treatment with 3.5 g. (0.04 mole) of acetyl chloride at room temperature for 3 days. The reaction mixture is evaporated, treated with benzene, evaporated to dryness, and the process repeated once more with benzene, twice with toluene and twice with petroleum ether. There is afforded N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride, m.p. 70° to 77° C.

出典