Water → HCID 14835341, compound

HRID 1198977Notes

Reaction equation

HRID 1198977 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][N:12]=[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[CH:6][CH:5]=1.[C-]#[N:20].[K+].O.O1CCOCC1>C(Cl)Cl>[N:12]1[O:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH2:3][C:2]#[N:20])=[CH:5][CH:6]=2)=[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=12

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 21761090HCID 21761090, compound

Product 1

HCID 14835341HCID 14835341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 11.1 g (0.039 mole) of 3-[4-(bromoethyl)phenyl]-2,1-benzisoxazole, 13.0 g (0.2 mole) of potassium cyanide, 55 ml of water and 80 ml of dioxane was heated at reflux under a nitrogen atmosphere for 2 hrs. The mixture was cooled, 200 ml of methylene chloride was added and the layers were separated. The organic layer was washed twice with water, dried over sodium sulfate and concentrated to give a gummy solid as residue. The residue was chromatographed on 150 g of silica gel and the product was eluted with 10% methanol in benzene to yield 4.4 g (48%) of solid, m.p. 118°-121° C. (after recrystallization from 2-propanol, charcoal).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 2 hrs
  3. temperatureThe mixture was cooled
  4. customthe layers were separated
  5. washThe organic layer was washed twice with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a gummy solid as residue
  9. customThe residue was chromatographed on 150 g of silica gel
  10. washthe product was eluted with 10% methanol in benzene
  11. customto yield
  12. custom4.4 g (48%) of solid, m.p. 118°-121° C. (after recrystallization from 2-propanol, charcoal)

Sources & evidence

ORD record
ord-aa3cccf0e39f409f811f601ab8307794
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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