Iodine → HCID 70654305, compound

HRID 1472230Notes

Reaction equation

HRID 1472230 reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[S:22])[CH2:15][CH2:16][CH2:17][CH:18]=[C:19]([CH3:21])[CH3:20])=[CH:9][CH:8]=1.II.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]=[C:14]2[CH2:15][CH2:16][CH2:17][C:18](=[C:19]([CH3:20])[CH3:21])[S:22]2)=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-eneHCID 86670260HCID 86670260, compound

Product 1

HCID 70654305HCID 70654305, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a tetrahydrofuran (40 ml) solution of 6-methyl-5-heptenethioic acid (4-chloro-phenyl)-amide (2.0 g), a tetrahydrofuran (15 ml) solution of iodine (2.3 g) was added dropwise at 0° C. The temperature was raised to room temperature, followed by stirring overnight. After cooling to 0° C., a tetrahydrofuran (5 ml) solution of diazabicycloundecene (2.9 g) was added dropwise. After raising the temperature to room temperature and further stirring for 1 hour, 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 1.1 g of the target compound.

Workup

  1. temperatureAfter cooling to 0° C.
  2. temperatureAfter raising the temperature to room temperature
  3. stirringfurther stirring for 1 hour
  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-46d82d2961b644429536dd6d165fb0af
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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