Iodine → HCID 68518803, compound

HRID 732832Notes

Reaction equation

HRID 732832 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([O:14][C:15]1[CH:20]=[CH:19][C:18](N)=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH:8]=[CH:7]2.[I:32]I.C(ON=O)CC(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C.[Cu](I)I.C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10]([O:14][C:15]1[CH:20]=[CH:19][C:18]([I:32])=[CH:17][CH:16]=1)=[C:9]([C:22]1[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=1)[CH:8]=[CH:7]2

Participants

8

Reactant 4

HCID 807IodineHCID 8053Isoamyl NitriteHCID 24477Sodium ThiosulfateHCID 68519557HCID 68519557, compound

Product 1

HCID 68518803HCID 68518803, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Place 6-methoxy-2-(4-methanesulfonylphenyl)-1-(4-aminophenoxy)naphthalene hydrochloride (1 eq.), iodine (0.6 eq.), copper iodide (1.05 eq.) and acetonitrile in a 3 neck flask equipped with a mechanical stirrer, addition funnel, nitrogen purge and temperature probe. Charge the addition funnel with isoamylnitrite (1.1 eq.) in acetonitrile and add this mixture dropwise at 20° C. or below. After the addition, stir the mixture for 1 hour. Once the reaction is complete, add saturated sodium thiosulfate and methylene chloride to the mixture and stir for 1 hour. Filter the reaction mixture and separate the layers. Concentrate the organic layer to form a solid. Purify the solid on silica gel to afford the title compound.

Workup

  1. customnitrogen purge
  2. additionadd this mixture dropwise at 20° C. or below
  3. additionAfter the addition
  4. stirringstir for 1 hour
  5. filtrationFilter the reaction mixture
  6. customseparate the layers
  7. concentrationConcentrate the organic layer
  8. customto form a solid
  9. customPurify the solid on silica gel

Sources & evidence

ORD record
ord-bf30fe7d6cc1476caa4a9be6684ee581
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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