Benzyl mercaptan → 4-(2-Benzylsulfanyl-ethyl)-5-(4-bromo-phenyl)-3-methyl-isoxazole

HRID 1512595Notes

Reaction equation

HRID 1512595 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:22][N:21]=[C:20]([CH3:23])[C:19]=2[CH2:24][CH2:25]OS(C)(=O)=O)=[CH:14][CH:13]=1>CCO.CCOC(C)=O.O>[CH2:1]([S:8][CH2:25][CH2:24][C:19]1[C:20]([CH3:23])=[N:21][O:22][C:18]=1[C:15]1[CH:16]=[CH:17][C:12]([Br:11])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 86652398Methanesulfonic acid 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]ethyl ester

Product 1

HCID 665772304-(2-Benzylsulfanyl-ethyl)-5-(4-bromo-phenyl)-3-methyl-isoxazole

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

Benzyl mercaptan (0.06 mL, 0.45 mmol) and sodium hydroxide (0.030 g, 0.76 mmol) were combined in EtOH. Methanesulfonic acid 2-[5-(4-bromo-phenyl)-3-methyl-isoxazol-4-yl]-ethyl ester (0.161 g, 0.45 mmol) was added and the reaction was stirred at 70° C. for 2 hours. The mixture was diluted with EtOAc and H2O and separated. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered, and concentrated to give the title compound.

Workup

  1. customseparated
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dad9f40b556e46caae0cc6fc1433e4f4
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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