Ethanol → 4-(3-(1-Phenylethyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

HRID 383229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 383229
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH2:7][O:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11](O)[CH:10]=3)=[CH:4][CH:3]=1.[CH3:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:28]=[O:29].[CH2:30](O)C>>[C:22]1([CH:21]([N:20]2[CH2:19][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][C:11]=3[O:29][CH2:28]2)[O:8][CH2:7][C:6]([C:5]2[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:15]4)[CH3:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 4

HCID 702Ethanol2×HCID 712FormaldehydeHCID 7669N-MethylbenzylamineHCID 219100Phenoxodiol2×

Produkt 1

HCID 248965814-(3-(1-Phenylethyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

4′,7-Dihydroxyisoflav-3-ene (0.45 g, 1.87 mmol) was dissolved in ethanol (ca 40 mL) and heated to 80-90° C. A solution of methylbenzylamine (0.44 mL, 4.03 mmol) and 37% formaldehyde (0.35 mL, 123 mmol) in ethanol (ca. 20 mL) was added to the dehydroequol solution. The reaction mixture was refluxed for approximately 7 hours and after cooling to room temperature the volume was concentrated in vacuo. The mixture was left in the fridge to crystallise. The yellow solid was collected under suction and the filtrate evaporated to dryness to obtain a second crop of the title compound, (combined yield 0.17 g, 23%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for approximately 7 hours
  2. temperatureafter cooling to room temperature the volume
  3. concentrationwas concentrated in vacuo
  4. waitThe mixture was left in the fridge
  5. customto crystallise
  6. customThe yellow solid was collected under suction
  7. customthe filtrate evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-b6c6448adf474d74b28f8268ff7e64f2
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367659B2

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