Formaldehyde → HCID 23368468, compound

HRID 1901613Notes

Reaction equation

HRID 1901613 reaction equation
N[CH:2]([CH2:15][O: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.[C:18]1(C)C=CC(S(O)(=O)=O)=CC=1.C=O.[C:31]([BH3-])#[N:32].[Na+].[OH-].[Na+]>C(OCC)(=O)C.O>[ClH:14].[Cl:14][C:11]1[CH:12]=[CH:13][C:8]2[O:7][N:6]=[C:5]([O:4][CH2:3][CH:2]([N:32]([CH3:31])[CH3:18])[CH2:15][O:16][CH3:17])[C:9]=2[CH:10]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23368365HCID 23368365, compound

Product 1

HCID 23368468HCID 23368468, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.50 g of 3-(2-amino-3-methoxypropoxy)-5-chloro-1,2-benzoisoxazole are added 0.41 g of p-toluenesulfonic acid and 0.34 ml of 37% formalin, and 0.26 g of sodium cyanoborohydride is then added at 15°-20° C., after which they are subjected to reaction at the same temperature for one hour. Water and ethyl acetate are added to the reaction mixture, and the pH is adjusted to 10 with a 10% (w/w) aqueous sodium hydroxide solution and the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which 0.89 ml of a dioxane solution (2.2N) of hydrogen chloride is added. The crystals precipitated are collected by filtration and recrystallized from a mixed solvent of acetone and methanol, to obtain 0.35 g of colorless, crystalline 5-chloro-3-(2-dimethylamino-3-methoxypropoxy)-1,2-benzoisoxazole hydrochloride having a melting point of 163°-164° C.

Workup

  1. additionis then added at 15°-20° C.
  2. customafter which they are subjected to reaction at the same temperature for one hour
  3. customthe organic layer is separated
  4. washThe separated organic layer is washed with a saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. additionafter which 0.89 ml of a dioxane solution (2.2N) of hydrogen chloride is added
  7. customThe crystals precipitated
  8. filtrationare collected by filtration
  9. customrecrystallized from a mixed solvent of acetone and methanol

Sources & evidence

ORD record
ord-3627f8b5ecd340b5af152827e75ab9b3
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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