2-Amino-2-methyl-1-propanol → HCID 23368464, compound

HRID 1901651Notes

Reaction equation

HRID 1901651 reaction equation
[H-].[Na+].[NH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].Cl[C:10]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[O:12][N:11]=1>O1CCCC1>[NH2:3][C:4]([CH3:8])([CH3:7])[CH2:5][O:6][C:10]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[O:12][N:11]=1

Participants

5

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 24758Sodium hydrideHCID 135684483,5-Dichloro-1,2-benzoxazole

Product 1

HCID 23368464HCID 23368464, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of 0.43 g of 60% (w/w) sodium hydride in 15 ml of tetrahydrofuran is added a solution of 0.80 g of 2-amino-2-methyl-1-propanol in 20 ml of tetrahydrofuran at 20°-25° C., and they are refluxed for two hours. To the reaction mixture is added a solution of 2.36 g of 3,5-dichloro-1,2-benzoisoxazole in 20 ml of tetrahydrofuran under reflux, and they are refluxed for a further one hour. After cooling, the solvent is removed by distillation under reduced pressure, and 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 then purified by a column chromatography [eluant:chloroform:methanol=20:1], to obtain 1.59 g of oily 3-(2-amino-2-methylpropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. temperaturethey are refluxed for two hours
  2. temperatureunder reflux
  3. temperaturethey are refluxed for a further one hour
  4. temperatureAfter cooling
  5. customthe solvent is removed by distillation under reduced pressure, and ethyl acetate and water
  6. additionare 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 column chromatography [eluant:chloroform:methanol=20:1]

Sources & evidence

ORD record
ord-46f31d46de26414f8aae5d62dd19e611
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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