Sodium Iodide → HCID 178503134, compound

HRID 1515380Notes

Reaction equation

HRID 1515380 reaction equation
CS(Cl)(=O)=O.C(Cl)Cl.O[CH2:10][CH2:11][CH2:12]/[C:13](=[CH:23]\[S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)/[C:14](=[S:22])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[I-].[Na+]>O.C(N(CC)CC)C>[C:25]1([S:24]/[CH:23]=[C:13]2/[C:14](=[N:15]/[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)/[S:22][CH2:10][CH2:11][CH2:12]/2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 86658455HCID 86658455, compound

Product 1

HCID 178503134HCID 178503134, compoundYield 60.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

0.48 g of methanesulfonyl chloride was added to 20 ml of methylene chloride solution including 0.4 g of (E)-5-hydroxy-N-phenyl-2-(phenylthiomethylene) pentanethioamide, 0.46 g of triethylamine and 0.69 of sodium iodide. The resulting solution was stirred at room temperature for 3 hours, and added with water, extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.23 g of the title compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-774c043e58e84892b41ea0156ac02895
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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