Ethyl Acetate → 4-Tert-butylbenzoyl isothiocyanate

HRID 589313Notes

Reaction equation

HRID 589313 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[S-:14][C:15]#[N:16].[NH4+].C(OCC)(=O)C>CC(C)=O>[C:1]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([N:16]=[C:15]=[S:14])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 15666Ammonium thiocyanateHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 27953844-Tert-butylbenzoyl isothiocyanateYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 4-tert-butylbenzoyl chloride (6 g, 198 mmol) in acetone (250 mL) was added ammonium thiocynate (28 g, 237 mmol). The resulting yellow suspension was stirred at room temperature for 2 hours, condensed to dryness and then reconstituted through the addition of ethyl acetate (200 mL). The organic portion was washed with a saturated sodium bicarbonate solution (2×200 ml) and brine (200 mL). The resulting organic phase was dried over anhydrous sodium sulfate and concentrated to a sticky liquid. The residue was chilled in a −10° C. freezer to give 37 grams of Intermediate A as a yellow solid (88%).

Workup

  1. customcondensed to dryness
  2. washThe organic portion was washed with a saturated sodium bicarbonate solution (2×200 ml) and brine (200 mL)
  3. dry with materialThe resulting organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated to a sticky liquid
  5. temperatureThe residue was chilled in a −10° C. freezer

Sources & evidence

ORD record
ord-8f942a98bfef478bb7ff16aff24a4688
Source dataset
uspto-grants-2016_01
Patent number
US09233087B2

Reaction notes

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