Sodium hydride → HCID 23368395, compound

HRID 1901633Notes

Reaction equation

HRID 1901633 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][CH3:7])[CH2:3][OH:4].[H-].[Na+].Cl[C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][N:12]=1>O1CCCC1>[NH2:1][CH:2]([CH2:5][CH2:6][CH3:7])[CH2:3][O:4][C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][N:12]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2490172-Amino-1-pentanolHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 23368395HCID 23368395, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2.86 g of 2-amino-1-pentanol in 2 ml of tetrahydrofuran is added to a suspension of 2.24 g of 60% (w/w) sodium hydride in 20 ml of tetrahydrofuran at 20°-25° C. and they are refluxed for two hours. Subsequently, under reflux, a solution of 4.3 g of 3-chloro-1,2-benzoisoxazole in 30 ml of tetrahydrofuran is added and refluxed for a further one hour. After cooling, the solvent is removed by distillation under reduced pressure. Ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and thereafter purified by a silica gel column chromatography [eluant:chloroform:methanol=20:1], to obtain 5.38 g of oily 3-(2-aminopentyloxy)-1,2-benzoisoxazole.

Workup

  1. temperaturethey are refluxed for two hours
  2. temperatureSubsequently, under reflux
  3. temperaturerefluxed for a further one hour
  4. temperatureAfter cooling
  5. customthe solvent is removed by distillation under reduced pressure
  6. additionEthyl acetate and water are added to the residue
  7. customobtained
  8. customthe organic layer is separated
  9. washThe separated organic layer is washed with a saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. custompurified by a silica gel column chromatography [eluant:chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-60157123800d44fc9ae728d5a512a247
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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