1,2-Benzisoxazole, 3-(bromomethyl)- → 3-[(5-(3-hydroxypropyl)-1H-imidazol-1-yl)methyl]-1,2-benzisoxazole

HRID 1032332

Reaktionsgleichung

Reaktionsgleichung von HRID 1032332
CN(C)C([N:5]1[CH:9]=[C:8]([CH2:10][CH2:11][CH2:12][O:13][Si](C)(C)C)[N:7]=[CH:6]1)=O.Br[CH2:20][C:21]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[O:23][N:22]=1.C[O-].[Na+]>C(#N)C.CO>[OH:13][CH2:12][CH2:11][CH2:10][C:8]1[N:7]([CH2:20][C:21]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[O:23][N:22]=2)[CH:6]=[N:5][CH:9]=1

Komponenten

6

Edukt 3

HCID 34991891,2-Benzisoxazole, 3-(bromomethyl)-HCID 10942334Sodium MethoxideHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Produkt 1

HCID 221656643-[(5-(3-hydroxypropyl)-1H-imidazol-1-yl)methyl]-1,2-benzisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution containing 1-dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)-imidazole (6.7 g, 0.025 mole), and 3-bromomethyl-1,2-benzisoxazole (5.3 g, 0.025 mole) in anhydrous acetonitrile (30 mL) is stirred at reflux for 72 hours. The reaction mixture is cooled and mixed with a solution of sodium methoxide (3 g, 0.055 mole) in methanol (30 mL). The resulting solution is stirred at reflux for 26 hours. The solvents are evaporated and the residue is taken up in 1N hydrochloric acid (30 mL). This solution is allowed to stand at ambient temperature for 3 hours and is then made basic (pH 9) by addition of 50% aqueous sodium hydroxide solution. The mixture is extracted with methylene chloride (2×25 mL) and the combined extracts are washed with water (2×20 mL), dried over anhydrous sodium sulfate, filtered, and the solvent is evaporated to give crude 3-[(5-(3-hydroxypropyl)-1H-imidazol-1-yl)-methyl]-1,2-benzisoxazole which is purified by trituration with acetone (15 mL), m.p. 129-131° C. The compound forms a hydrochloride hemihydrate, m.p. 155-157° C. when its solution in isopropanol is treated with ethereal hydrogen chloride.

Aufarbeitung

  1. temperatureat reflux for 72 hours
  2. temperatureThe reaction mixture is cooled
  3. stirringThe resulting solution is stirred
  4. temperatureat reflux for 26 hours
  5. customThe solvents are evaporated
  6. additionby addition of 50% aqueous sodium hydroxide solution
  7. extractionThe mixture is extracted with methylene chloride (2×25 mL)
  8. washthe combined extracts are washed with water (2×20 mL)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-cda90b1813424962a10a6017c256dc76
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04957931

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