4-Aminothiophenol → 4-[(Isoxazol-5-ylmethyl)sulfanyl]aniline

HRID 856752Notes

Reaction equation

HRID 856752 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Br[CH2:12][C:13]1[O:17][N:16]=[CH:15][CH:14]=1>CO.O>[O:17]1[C:13]([CH2:12][S:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=[N:16]1

Participants

6

Reactant 3

HCID 145104-AminothiophenolHCID 14798Sodium HydroxideHCID 100349035-(Bromomethyl)-1,2-oxazole

Product 1

HCID 432994194-[(Isoxazol-5-ylmethyl)sulfanyl]anilineYield 99.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

To a mixed solution of 4-aminothiophenol (600 mg) and sodium hydroxide (276 mg) in methanol (10 ml) and water (6 ml), a solution of 5-bromomethyl isoxazole (932 mg) in methanol (5 ml) was added at 0° C. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, to give 4-[(isoxazol-5-ylmethyl)sulfanyl]aniline (988 mg) as oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-61d16c8ca2d7496e8e7a1d478271e6c0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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