Acetyl chloride → HCID 19596644, compound

HRID 612931Notes

Reaction equation

HRID 612931 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:19])[CH3:18].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:19])[CH3:18]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 98595963-(2-Aminoethoxy)-5-phenylisoxazole hydrochloride

Product 1

HCID 19596644HCID 19596644, compoundYield 91.6%

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. Acetyl chloride (94 mg) and triethylamine (243 mg) were added thereto, and the resulting mixture was stirred 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 crystals thus obtained were recrystallized from ethyl acetate to obtain the title compound (225 mg, 91%) 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 crystals thus obtained
  6. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-84ef6243f83242e7bb262a067f2fb6ff
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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