Benzoyl chloride → 3-(2-Benzoylaminoethoxy)-5-phenylisoxazole

HRID 612932Notes

Reaction equation

HRID 612932 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][N:7]=1.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>O1CCCC1>[C:17]([NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:8][N:7]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 98595963-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride

Product 1

HCID 195966643-(2-Benzoylaminoethoxy)-5-phenylisoxazoleYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

3-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride (240 mg) was suspended in anhydrous tetrahydrofuran (5 ml), and the suspension was cooled to 5° C. Benzoyl chloride (168 mg) and triethylamine (243 mg) were added thereto, followed by stirring of the resulting mixture at the same temperature for 30 minutes. At the end of this time, the reaction mixture was added to ice-cold water (40 ml) and extracted with ethyl acetate (40 ml×2). Then, the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was recrystallized from ethyl acetate to obtain the title compound (276 mg, 90%) as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate (40 ml×2)
  2. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-a09716455e2541fbafea726a764f1c90
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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