Potassium Carbonate → HCID 59739561, compound

HRID 1192954Notes

Reaction equation

HRID 1192954 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:10])=[N:5][S:6][C:7]=1[C:8]#[N:9].NC(N)=S.C[S:16]([C:19]1[CH2:23][C:22]([CH3:25])([CH3:24])[O:21][N:20]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:24][C:22]1([CH3:25])[O:21][N:20]=[C:19]([S:16][CH2:2][C:3]2[C:4]([CH3:10])=[N:5][S:6][C:7]=2[C:8]#[N:9])[CH2:23]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazolineHCID 59739560HCID 59739560, compound

Product 1

HCID 59739561HCID 59739561, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromomethyl-5-cyano-3-methyl-isothiazole (50% purity) (0.65 g, 1.5 mmol) was dissolved in ethanol (30 ml) and thiourea (242 mg, 3.2 mmol) was added. The mixture was stirred at room temperature until the solids were dissolved. 3-Methane-sulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (540 mg, 3.2 mmol) and potassium carbonate (440 mg, 3.2 mmol) were added and the mixture was heated under reflux for 1 hour. The solids were removed by filtration and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (0.25 g, 62% yield). 1H-NMR (400 MHz, CDCl3): 1.44 (6H, s, Me), 2.6 (3H, s, Me), 2.8 (2H, s, CH2), 4.4 (2H, s, CH2).

Workup

  1. dissolutionwere dissolved
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ac45458b58ef4ad58453bf0928ba491c
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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