Salicylic Acid → HCID 54122933, compound

HRID 992844Notes

Reaction equation

HRID 992844 reaction equation
[NH:1]1[C:8](=[O:9])[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[C:10](O)(=O)[C:11]1[C:12](=CC=[CH:16][CH:17]=1)[OH:13].[Se](=O)=O.[C:23](OO)(C)([CH3:25])[CH3:24]>ClCCl.C1C=CC=CC=1>[OH:13][CH2:12][C:11]([CH3:10])=[CH:17][CH2:16][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 54122933HCID 54122933, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the barbituric acid derivative prepared in the preceding experiment (100 mg, 0.42 mmol) in 1.0 mL dichloromethane was added 6 mg (42 umol) salicylic acid and 9 mg (84 umol) selenium dioxide. The suspension was placed in a water bath, and 0.29 mL (3.8M, 1.09 mmol) of a anhydrous solution of tert-butyl hydroperoxide in benzene was added. The suspension was then vigorously stirred for 12 hours at ambient temperature. The reaction mixture was concentrated, and chromatographed directly on a silica gel column, eluting with 40%, 50%, 60%, and 70% ethyl acetate/hexane. In addition to some starting material as well as other products, 21 mg of a colorless oil was isolated.

Workup

  1. customThe suspension was placed in a water bath
  2. concentrationThe reaction mixture was concentrated
  3. customchromatographed directly on a silica gel column
  4. washeluting with 40%, 50%, 60%, and 70% ethyl acetate/hexane
  5. additionIn addition to some starting material as well as other products

Sources & evidence

ORD record
ord-d4d13ee9430a4adba8474dd044646faf
Source dataset
uspto-grants-2002_10
Patent number
US06472227B1

Reaction notes

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