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

HRID 1032332노트

반응식

HRID 1032332 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cda90b1813424962a10a6017c256dc76
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04957931

반응 노트

불러오는 중…