Iodine → HCID 24756814, compound

HRID 643648Notes

Reaction equation

HRID 643648 reaction equation
F[C:2]1[CH:22]=[CH:21][C:5]2[N:6]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=4)[N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1.[I:23]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[I:23][C:2]1[CH:22]=[CH:21][C:5]2[N:6]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=4)[N:9]=[C:7]3[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 24757875HCID 24757875, compound

Product 1

HCID 24756814HCID 24756814, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5 (64 mg, 1 eq) was dissolved in CH2Cl2 (5 ml) and to that was added dropwise I2 (39 mg, 1.1 eq) in 2 ml of CH2Cl2, the resulting mixture was stirred at RT for 1 h before hydrolysis with 5 ml of Na2S2O3 10%. Extraction was performed using CH2Cl2 (2×5 ml) with drying over Na2SO4 and concentrating was carried out in vacuum. Purification by flash chromatography (SiO2, hexane/AcOEt, 9/1) was used to give 6 as a white solid in 15% yield.

Workup

  1. extractionExtraction
  2. dry with materialwith drying over Na2SO4
  3. concentrationconcentrating
  4. customPurification by flash chromatography (SiO2, hexane/AcOEt, 9/1)

Sources & evidence

ORD record
ord-086b877479574b50a3a304d099ce91b1
Source dataset
uspto-grants-2010_04
Patent number
US07700616B2

Reaction notes

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