Potassium Carbonate → HCID 59739616, compound

HRID 1192963Notes

Reaction equation

HRID 1192963 reaction equation
NC(N)=S.Br[CH2:6][C:7]#[C:8][CH3:9].C[S:11]([C:14]1[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][N:15]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:6]([S:11][C:14]1[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][N:15]=1)[C:7]#[C:8][CH3:9]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 27568621-Bromo-2-butyneHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazoline

Product 1

HCID 59739616HCID 59739616, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (2.15 g, 28.21 mmol) was added to a solution of 1-bromo-2-butyne (2.47 ml, 28.21 mmol) in ethanol (69 ml) and the solution was heated under reflux for 1 hour 40 minutes. The mixture was allowed to cool to room temperature and 3-methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (5 g, 28.21 mmol) and potassium carbonate (4.28 g, 31.03 mmol) were added. The mixture was heated under reflux for 2 hours 35 minutes and allowed to cool to room temperature. The mixture was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (3.085 g, 60% yield) as a pale yellow oil. 1H-NMR (400 MHz, CDCl3): 1.42 (6H, s, Me), 1.83 (3H, t, Me), 2.81 (2H, s, CH2), 3.77 (2H, q, CH2).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 hour 40 minutes
  3. temperatureThe mixture was heated
  4. temperatureunder reflux for 2 hours 35 minutes
  5. temperatureto cool to room temperature
  6. customThe mixture was partitioned between water and ethyl acetate
  7. extractionThe aqueous phase was extracted with ethyl acetate
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8a30b75233104a66969dedc68a03001d
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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