Sodium Iodide → HCID 22176584, compound

HRID 1797201Notes

Reaction equation

HRID 1797201 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]#[N:30].[Na+].[I-]>CN(C=O)C.O>[OH:1][C:2]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:16][CH:17]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 22176571HCID 22176571, compound

Product 1

HCID 22176584HCID 22176584, compoundYield 107.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Into a 250 mL-3 neck flask fitted with a stirrer and thermometer, 400 mg of [2-hydroxy-2-(4-hydroxyphenyl)propyl][(methylethyl)sulfonyl]amine in DMF (10 mL) was added dropwise to 40 mg of NaH in DMF (30 mL) while stirring at room temperature under a nitrogen atmosphere. After stirring at this temperature for 30 minutes, 290 mg of alpha-bromo 2-cyanotoluene in DMF (10 mL) was added dropwise followed by the addition of 184 mg of NaI portion wise. The reaction was then heated at 100° C. for 2 hours. The mixture was cooled to room temperature and poured into H2O and the desired product was extracted with ethyl acetate. This organic layer was washed with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 612 mg of a brown oil. This material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of hexane/ethyl acetate 1:1 to yield intermediate title compound (161 mg, 28%) as a viscous oil. Ion spray M.S. 387.9 (M*−1).

Workup

  1. customInto a 250 mL-3 neck flask fitted with a stirrer
  2. stirringAfter stirring at this temperature for 30 minutes
  3. temperatureThe reaction was then heated at 100° C. for 2 hours
  4. temperatureThe mixture was cooled to room temperature
  5. extractionthe desired product was extracted with ethyl acetate
  6. washThis organic layer was washed with H2O
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-e189905c680c4f968025e5dbb699f5a0
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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