Sodium Hypochlorite → HCID 178516689, compound

HRID 1037394Notes

Reaction equation

HRID 1037394 reaction equation
[I:1][C:2]1[C:3](=[O:21])[C:4]2[C:9]([O:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:8]1[NH:18][N:19]=[CH:20][C:7]1=[CH:6][CH:5]=2.[Cl:22][O-].[Na+]>CCO>[Cl:22][C:20]1[C:7]2=[CH:6][CH:5]=[C:4]3[C:9]([O:10][C:11]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[C:2]([I:1])[C:3]3=[O:21])=[C:8]2[NH:18][N:19]=1

Participants

4

Reactant 2

HCID 23665760Sodium HypochloriteHCID 670677727-Iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one

Product 1

HCID 178516689HCID 178516689, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 7-iodo-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one (73 mg, 0.188 mmol) in EtOH (10 mL), with cooling in a 10° C. water bath, was added sodium hypochlorite (10% aqueous solution, 9 mL). After 15 minutes, the temperature was allowed to increase to RT. After a further 30 minutes, the reaction mixture was concentrated in vacuo and the remaining reside was partitioned between EtOAc and water. The resulting biphasic mixture was separated, the aqueous phase was further extracted with EtOAc, the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and evaporated in vacuo to afford the title compound (44 mg, 55%) as a cream solid. LCMS (Method H): RT=3.75 min, [M+H]+=423/425.

Workup

  1. waitAfter a further 30 minutes
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customthe remaining reside was partitioned between EtOAc and water
  4. customThe resulting biphasic mixture was separated
  5. extractionthe aqueous phase was further extracted with EtOAc
  6. washthe combined organic extracts were washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-53a038332a904e4f87c96bf7949dec11
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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