Iodine → HCID 70654446, compound

HRID 1472235Notes

Reaction equation

HRID 1472235 reaction equation
O1CCCC1.[C:6]1([CH3:22])[CH:11]=[CH:10][C:9]([NH:12][C:13](=[S:21])[CH2:14][CH2:15][C:16]([CH3:20])([CH3:19])[CH:17]=[CH2:18])=[CH:8][CH:7]=1.II.C1CCN2C(=NCCC2)CC1>O>[CH3:20][C:16]1([CH3:19])[C:17](=[CH2:18])[S:21][C:13](=[N:12][C:9]2[CH:8]=[CH:7][C:6]([CH3:22])=[CH:11][CH:10]=2)[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86670262HCID 86670262, compound

Product 1

HCID 70654446HCID 70654446, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a tetrahydrofuran (25 ml) solution of 4,4-dimethyl-5-hexenethioic acid p-tolylamide (1.2 g), a tetrahydrofuran (10 ml) solution of iodine (1.5 g) was added dropwise at 0° C., followed by raising the temperature to room temperature and further stirring overnight. After cooling to 0° C., a tetrahydrofuran (3 ml) solution of DBU (1.8 g) was added dropwise. After raising the temperature to room temperature and further stirring overnight, water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.53 g of the target compound.

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperatureAfter raising the temperature to room temperature
  3. stirringfurther stirring overnight
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-31e189fe204f4037a0b84a909baa4af4
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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