Acetone → HCID 24960260, compound

HRID 1694658Notes

Reaction equation

HRID 1694658 reaction equation
O[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:13]1[CH:18]=CC=C[CH:14]=1)=[C:6](O)[O:7]2.Cl[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1)=[O:23].[OH-:35].[K+].[CH3:37][C:38]([CH3:40])=[O:39]>>[OH:39][C:38]1[CH:40]=[CH:18][C:13]([C:5]2[C:4](=[O:19])[C:3]3[C:8](=[CH:9][C:10]([O:35][CH2:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=4)=[O:23])=[CH:11][CH:2]=3)[O:7][CH:6]=2)=[CH:14][CH:37]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 7367442-chloro-N-[3-(trifluoromethyl)phenyl]acetamideHCID 178515329HCID 178515329, compound

Product 1

HCID 24960260HCID 24960260, compound

Procedure

Dihydroxyisoflavone (0.2 g, 0.78 mmol) was suspended in acetone (10 ml), and to this suspension was added 2-chloro-N-[3-(trifluoromethyl)phenyl]acetamide (0.18 g, 0.78 mmol) and 11% potassium hydroxide (0.78 mmol). The mixture was refluxed for 24 hours, and the solvent removed under reduced pressure. The residue was treated with water, sonicated, filtered, and air-dried. The solid was triturated with methanol, filtered, to afford 2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yloxy]-N-[3-(trifluoromethyl)phenyl]acetamide. If desired, the product may be further purified by preparative thin layer chromatography, eluting with dichloromethane/methanol 15/1.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customthe solvent removed under reduced pressure
  3. additionThe residue was treated with water
  4. customsonicated
  5. filtrationfiltered
  6. customair-dried
  7. customThe solid was triturated with methanol
  8. filtrationfiltered

Sources & evidence

ORD record
ord-bb8da65b8b00426e86479bc11f57b3e0
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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