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

HRID 1528818Notes

Reaction equation

HRID 1528818 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-3932c4963d584cafb08912dddae48053
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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