Salicylic Acid → HCID 70151236, compound

HRID 2371853Notes

Reaction equation

HRID 2371853 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Se](=O)=O.[C:13](O)(=O)[C:14]1[C:15](=CC=[CH:19][CH:20]=1)[OH:16].[C:23](OO)(C)([CH3:25])[CH3:24]>ClCCl.C1C=CC=CC=1>[OH:16][CH2:15]/[C:14](/[CH3:13])=[CH:20]/[CH2:19][C:7]1([CH2:25][CH:23]=[CH2:24])[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][C:8]1=[O:9]

Participants

7

Reactant 4

HCID 338Salicylic AcidHCID 6211Barbituric AcidHCID 6410tert-Butyl hydroperoxideHCID 24007Selenium Dioxide

Product 1

HCID 70151236HCID 70151236, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the 100 mg dienic barbituric acid prepared according to the immediately preceding Example, in 1 mL dichloromethane, was added 9 mg (84 μmol) selenium dioxide, 6 mg (42 μmol) salicylic acid, and 0.29 mL (1.09 mmol) of a 3.8 M solution of t-butylhydroperoxide in benzene. The solution was stirred well for 12 hr and concentrated. Chromatography on a 1×14 cm column, packed with 30% ethyl acetate/hexane and eluted with 25 mL each of 40%, 50%, 60%, and 70% ethyl acetate/hexane provided 21 mg of the desired product as a clear colorless oil in 7 mL fractions 14-19, as well as a mixture of starting material and an unidentified product in fractions 6-10.

Workup

  1. concentrationconcentrated
  2. washeluted with 25 mL each of 40%, 50%, 60%, and 70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7a834039dcfc49f9addcbfb339db8e43
Source dataset
uspto-grants-1992_03
Patent number
US05096838

Reaction notes

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