Potassium Carbonate → 5-(5,5-Dimethyl-4,5-dihydroisoxazol-3-ylsulfanylmethyl)-3-methoxy-isoxazole

HRID 1192957Notes

Reaction equation

HRID 1192957 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=1.NC(N)=S.C[S:15]([C:18]1[CH2:22][C:21]([CH3:24])([CH3:23])[O:20][N:19]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:23][C:21]1([CH3:24])[O:20][N:19]=[C:18]([S:15][CH2:2][C:3]2[O:7][N:6]=[C:5]([O:8][CH3:9])[CH:4]=2)[CH2:22]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 108454055-(Bromomethyl)-3-methoxy-1,2-oxazoleHCID 121376563-Methylsulfonyl-5,5-dimethyl-2-isoxazoline

Product 1

HCID 597395995-(5,5-Dimethyl-4,5-dihydroisoxazol-3-ylsulfanylmethyl)-3-methoxy-isoxazoleYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromomethyl-3-methoxy-isoxazole (1.22 g, 6.35 mmol) was dissolved in ethanol (30 ml) and thiourea (484 mg, 6.4 mmol) was added. The mixture was stirred at room temperature until the solids were dissolved. 3-Methanesulfonyl-5,5-dimethyl-4,5-dihydroisoxazole (1.08 g, 6.4 mmol) and potassium carbonate (880 mg, 6.4 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 as colourless oil (0.69 g, 45% yield over 3 steps).

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-1b84df4719be4e77bd721b89be15f453
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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