Water → HCID 15634757, compound

HRID 1198991Notes

Reaction equation

HRID 1198991 reaction equation
Br[CH2:2][C:3]1[C:11]2[C:7](=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[O:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1.[C-:18]#[N:19].[K+].O.O1CCOCC1>C(Cl)Cl>[C:12]1([C:8]2[O:9][N:10]=[C:11]3[C:3]([CH2:2][C:18]#[N:19])=[CH:4][CH:5]=[CH:6][C:7]=23)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 15634755HCID 15634755, compound

Product 1

HCID 15634757HCID 15634757, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 17.3 g (0.06 mole) of 7-bromomethyl-3-phenyl-2,1-benzisoxazole, 17 g of potassium cyanide, 80 ml of water and 120 ml of dioxane was heated at reflux under a nitrogen atmosphere for 2 hr. The mixture was then cooled and diluted with 300 ml of methylene chloride. The organic layer was separated, washed with water and dried over magnesium sulfate. The solvents were removed under vacuum and the residue was crystallized twice from absolute ethanol to give 10.3 g (74%) of yellow crystals, m.p. 125°-138° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 2 hr
  3. temperatureThe mixture was then cooled
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvents were removed under vacuum
  8. customthe residue was crystallized twice from absolute ethanol

Sources & evidence

ORD record
ord-496318277a2e4054a205223c1d9bf176
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…