Formaldehyde → 2H-1,3-Benzoxazine, 3,4-dihydro-3-(2-phenylethyl)-8-propoxy-

HRID 258810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 258810
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1O)[CH2:2][CH3:3].[CH2:12]=[O:13].[CH2:14]([NH2:22])[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O1CCOC[CH2:24]1>>[CH2:14]([N:22]1[CH2:24][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:1][CH2:2][CH3:3])[C:10]=2[O:13][CH2:12]1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 4

HCID 712FormaldehydeHCID 1001PhenethylamineHCID 312751,4-DioxaneHCID 80476o-Propoxyphenol

Produkt 1

HCID 30432792H-1,3-Benzoxazine, 3,4-dihydro-3-(2-phenylethyl)-8-propoxy-

Versuchsvorschrift

To 15 ml. of dioxane are added 3 g. of ortho-normalpropoxyphenol, 9 ml. of 37% of formalin and 2.4 g. of phenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is cooled to be crystallized. A small portion of ethanol is added to the crystals, followed by filtration. The procedure yields 3-phenethyl-8-normal-propoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needless melting at 84° C. Yield: 3.8 g.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureon reflux for 3 hours
  3. distillationdistilled
  4. customto remove the solvent under reduced pressure
  5. customThe residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4)
  6. temperatureThe resultant oily substance is cooled
  7. customto be crystallized
  8. additionA small portion of ethanol is added to the crystals
  9. filtrationfollowed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-9ebb803258dd412bb2171ee05ddcde09
Quelldatensatz
uspto-grants-1977_07
Patentnummer
US04035363

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