Sodium Hydroxide → HCID 23368378, compound

HRID 1901649Notes

Reaction equation

HRID 1901649 reaction equation
[NH2:1][CH:2]([CH2:15][CH2:16][CH3:17])[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1.[CH:18](OC(=O)C)=[O:19].[OH-].[Na+]>C(Cl)Cl>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][N:6]=[C:5]([O:4][CH2:3][CH:2]([NH:1][CH:18]=[O:19])[CH2:15][CH2:16][CH3:17])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 75269Acetic-formic anhydrideHCID 23368525HCID 23368525, compound

Product 1

HCID 23368378HCID 23368378, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g of 3-(2-aminopentyloxy)-5-chloro-1,2-benzoisoxazole in 10 ml of methylene chloride is added 0.42 g of acetic formic anhydride with ice-cooling, and they are subjected to reaction at room temperature for one hour. The solvent is removed by distillation under reduced pressure, and water and ethyl acetate are added to the residue obtained, and the pH is adjusted to 8 with a 20% (w/w) aqueous sodium hydroxide solution. After shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure, to obtain 1.1 g of colorless, crystalline 5-chloro-3-(2-formylaminopentyloxy)-1,2-benzoisoxazole having a melting point of 107.2°-108.3° C.

Workup

  1. temperaturecooling
  2. customthey are subjected to reaction at room temperature for one hour
  3. customThe solvent is removed by distillation under reduced pressure, and water and ethyl acetate
  4. additionare added to the residue
  5. customobtained
  6. customthe organic layer is separated
  7. washThe separated organic layer is washed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a565592b530842beba6628e373c90500
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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