반응 #549237

반응 방정식

1-chloro-2-hydroxy-3-phenoxypropane

acetate

acetyl chloride

trichloroacetamidine

→

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

용매

tetrahydrofuran

acetic acid

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The mixture is heated
2. 2
   온도at reflux for 3 hours
3. 3
   농축concentrated to an oil, which
4. 4
   세척washed well with water
5. 5
   건조The benzene layer is dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   workup.ADDITIONtreated with excess ethanolic hydrogen chloride
8. 8
   기타to provide the crude hydroxy amidine hydrochloride
9. 9
   기타The reaction mixture is evaporated
10. 10
    workup.ADDITIONtreated with benzene
11. 11
    기타evaporated to dryness

실험 절차

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.

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