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

HRID 383228Notes

Reaction equation

HRID 383228 reaction equation
[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.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:27]=[O:28].[CH2:29](O)C>>[CH2:19]([N:26]1[CH2:29][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][C:11]=2[O:28][CH2:27]1)[O:8][CH2:7][C:6]([C:5]1[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH:15]3)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 712FormaldehydeHCID 7504BenzylamineHCID 219100Phenoxodiol2×

Product 1

HCID 250064744-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

Conditions

Temperature
85 °C

Procedure

4′,7-Dihydroxyisoflav-3-ene (0.47 g, 1.97 mmol) was dissolved in ethanol (ca. 40 mL) and heated to 80-90° C. A solution of benzylamine (0.44 mL, 3.5 mmol) and 37% formaldehyde (0.35 mL, 12.7 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%).

Workup

  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

Sources & evidence

ORD record
ord-c6eb609a9c764f31bf1e3a52ab7d10d8
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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