Iodine → HCID 22931936, compound

HRID 2373336Notes

Reaction equation

HRID 2373336 reaction equation
[I:1]I.[CH3:3][CH:4]([C:9]1[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=1[NH2:11])[CH2:5][CH:6]([CH3:8])[CH3:7].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CO>[I:1][C:14]1[CH:13]=[CH:12][C:10]([NH2:11])=[C:9]([CH:4]([CH3:3])[CH2:5][CH:6]([CH3:7])[CH3:8])[CH:15]=1

Participants

6

Reactant 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 115284412-(1,3-Dimethylbutyl)aniline

Product 1

HCID 22931936HCID 22931936, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

In methanol was dissolved 2.53 g (10 mmol) of iodine, and 2-(1,3-dimethylbutyl)aniline (1.77 g, 10 mmol) was added thereto under ice-cooling, after which an aqueous solution of sodium hydrogencarbonate (1.26 g, 15 mmol) was added thereto and the resulting mixture was stirred at 0° C. for 4 hours. Sodium thiosulfate was added to the reaction mixture, and the resulting mixture was concentrated under reduced pressure, diluted with ethyl acetate and then washed with water. The organic layer was dried over magnesium sulfate and the residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 2.71 g of the desired compound.

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe residue was separated
  8. custompurified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-934e95f468eb49f3b79176e2186f92c4
Source dataset
uspto-grants-2008_12
Patent number
US07459477B2

Reaction notes

Loading…