p-Tolyl isothiocyanate → HCID 86670262, compound

HRID 1472234Notes

Reaction equation

HRID 1472234 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([N:7]=[C:8]=[S:9])=[CH:3][CH:2]=1.[CH3:11][C:12]([CH3:19])([CH:17]=[CH2:18])[CH2:13][CH2:14][Mg]Br.[Cl-].[NH4+]>O1CCCC1>[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([NH:7][C:8](=[S:9])[CH2:18][CH2:17][C:12]([CH3:19])([CH3:11])[CH:13]=[CH2:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 12149p-Tolyl isothiocyanateHCID 25517Ammonium ChlorideHCID 178443914HCID 178443914, compound

Product 1

HCID 86670262HCID 86670262, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a dehydrated tetrahydrofuran (30 ml) solution of p-tolyl isothiocyanate (1.8 g), a tetrahydrofuran solution of the above (3,3-dimethyl-4-pentenyl)magnesium bromide was added dropwise at 0° C., followed by stirring at 0° C. for 30 minutes. After raising the temperature to room temperature and further stirring for 30 minutes, an aqueous saturated ammonium chloride solution was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 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 1.2 g of the target compound.

Workup

  1. temperatureAfter raising the temperature to room temperature
  2. stirringfurther stirring for 30 minutes
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c5997a797cca453999841615d6ae4c07
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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