Iodine → HCID 57535429, compound

HRID 1455647Notes

Reaction equation

HRID 1455647 reaction equation
Br[C:2]1[CH:3]=[N+]([O-])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[I:19]I.N([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+].C[CH2:39][O:40][C:41]([CH3:43])=[O:42]>C(Cl)Cl.CC(O)=O>[I:19][C:7]1[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][C:43]([C:41]([O:40][CH3:39])=[O:42])=[CH:3][CH:2]=1

Participants

8

Reactant 6

HCID 807IodineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 23668193Sodium NitriteHCID 57535415HCID 57535415, compound

Product 1

HCID 57535429HCID 57535429, compound

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

To the amino from step 2 (1.0 eq) in CH2Cl2—AcOH (1:1) at −20° C. was added iodine (1.5 eq), KI (1.5 eq) followed by NaNO2 (1.2 eq). The reaction mixture was stirred at r.t. for 1 h, diluted with EtOAc, a solution of Na2CO3 and a solution Na2S2O3. The organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hexane:EtOAc, 30:20-20:30) afforded the title compound as a pale yellow solid.

Workup

  1. washThe organic extracts were washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-db9ec7ca692246bd858b6b473c7cb139
Source dataset
uspto-grants-2009_01
Patent number
US07482456B2

Reaction notes

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