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

HRID 383237Notes

Reaction equation

HRID 383237 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.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.[CH2:28]=[O:29].[CH2:30](O)C>>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:25]2[CH2:30][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)=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 660364-ChlorobenzylamineHCID 219100Phenoxodiol

Product 1

HCID 250075994-(3-(4-Chlorobenzyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenolYield 88%

Procedure

4′,7-Dihydroxyisoflav-3-ene (506 mg, 2.11 mmol) was dissolved in ethanol (8 ml). 4-Chlorobenzylamine (0.33 ml, 2.70 mmol) was added followed by formaldehyde solution (2 ml, 0.03 mol, 37% wt.). The reaction was stirred at room temperature for 4 days. The white precipitate was collected to afford the title compound (748 mg, 88%).

Workup

  1. customThe white precipitate was collected

Sources & evidence

ORD record
ord-8846c1463c7c44188ba99fb43d9feeb2
Source dataset
uspto-grants-2013_02
Patent number
US08367659B2

Reaction notes

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