Salicylic Acid → HCID 70151236, compound

HRID 2372532Notes

Reaction equation

HRID 2372532 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.[CH:13]1[CH:18]=[C:17]([C:19]([OH:21])=O)[C:16](O)=CC=1.[C:23](OO)(C)([CH3:25])[CH3:24]>ClCCl.C1C=CC=CC=1>[OH:21][CH2:19]/[C:17](/[CH3:16])=[CH:18]/[CH2:13][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) salicyclic acid, and 0.29 mL (1.09 mmol) of a 3.8M 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

Workup

  1. concentrationconcentrated
  2. washeluted with 25 mL each of 40%, 50%, 60%, and 70% ethyl acetate/hexane
  3. customprovided 21 mg of the

Sources & evidence

ORD record
ord-14db3993058642368682e2a1a1f264b4
Source dataset
uspto-grants-1992_03
Patent number
US05099020

Reaction notes

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