4-Chlorophenyl isothiocyanate → HCID 86658456, compound

HRID 1515381Notes

Reaction equation

HRID 1515381 reaction equation
[CH:1]1([CH2:7][CH2:8][Mg]Br)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]=[C:19]=[S:20])=[CH:14][CH:13]=1.[Cl-].[NH4+]>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[S:20])[CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 164804-Chlorophenyl isothiocyanateHCID 25517Ammonium ChlorideHCID 178419671HCID 178419671, compound

Product 1

HCID 86658456HCID 86658456, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The obtained THF solution of 2-(2-cyclohexene-1-yl)ethyl magnesium bromide was dropped into 25 ml of anhydrous THF solution including 1.8 g of p-chlorophenyl isothiocyanate at 0° C. The resulting solution was stirred at 0° C. for 30 minutes, and stirred at room temperature for an additional 30 minutes. The solution was added with saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous magnesium sulfate, filtered, concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 2.2 g of the title compound.

Workup

  1. customat 0° C
  2. stirringstirred at room temperature for an additional 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried with 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-66a98c1436dd44f3bb824e757347064a
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

Loading…