Reaktion #549237

Reaktionsgleichung

1-chloro-2-hydroxy-3-phenoxypropane

acetate

acetyl chloride

trichloroacetamidine

→

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

Lösungsmittel

tetrahydrofuran

acetic acid

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is heated
2. 2
   Temperaturat reflux for 3 hours
3. 3
   Einengenconcentrated to an oil, which
4. 4
   Waschenwashed well with water
5. 5
   TrocknenThe benzene layer is dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   workup.ADDITIONtreated with excess ethanolic hydrogen chloride
8. 8
   Sonstigeto provide the crude hydroxy amidine hydrochloride
9. 9
   SonstigeThe reaction mixture is evaporated
10. 10
    workup.ADDITIONtreated with benzene
11. 11
    Sonstigeevaporated to dryness

Vorschrift

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.

Quelle