Iodine → HCID 58470768, compound

HRID 1515382Notes

Reaction equation

HRID 1515382 reaction equation
C1COCC1.II.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[S:25])[CH2:17][CH2:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]2)=[CH:11][CH:10]=1>O>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]=[C:16]2[CH2:17][CH2:18][CH:19]3[CH:24]([CH:23]=[CH:22][CH2:21][CH2:20]3)[S:25]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 807IodineHCID 8028Tetrahydrofuran3×HCID 86658456HCID 86658456, compound

Product 1

HCID 58470768HCID 58470768, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 ml of THF solution including 2.4 g of iodine was added to 40 ml of THF solution including 2.2 g of N-(4-chlorophenyl)-3-(2-cyclohexene-1-yl) thiopropionamide at 0° C. The temperature was raised to room temperature and the resulting solution was stirred for one night. Then the temperature was cooled to 0° C., and 5 ml of THF solution including 4.1 g of 1,4 diazabicyclo[5,4,0]undec-7-ene(DBU) was dropped into the resulting solution. The solution was stirred at room temperature for one night, and added with water, and 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 0.84 of the title compound.

Workup

  1. customat 0° C
  2. temperatureThen the temperature was cooled to 0° C.
  3. additionwas dropped into the resulting solution
  4. stirringThe solution was stirred at room temperature for one night
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-070da7f4d167497bacb90cf49b9e2dae
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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