Water → 3-Phenyl-2,1-benzisoxazole-5-acetonitrile

HRID 1198982Notes

Reaction equation

HRID 1198982 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:17]=1)=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:9][N:10]=2.[C-:18]#[N:19].[K+].O.O1CCOCC1>C(Cl)Cl>[C:11]1([C:8]2[O:9][N:10]=[C:6]3[CH:5]=[CH:4][C:3]([CH2:2][C:18]#[N:19])=[CH:17][C:7]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 148353455-(Bromomethyl)-3-phenyl-2,1-benzisoxazole

Product 1

HCID 148353463-Phenyl-2,1-benzisoxazole-5-acetonitrileYield 114.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 9.1 g (0.032 mole) of 5-(bromomethyl)-3-phenyl-2,1-benzisoxazole, 9.8 g (0.15 mole) of potassium cyanide, 50 ml of water and 80 ml of dioxane was heated at reflux under nitrogen for 2.5 hr. The solution was cooled and diluted with 200 ml of methylene chloride. The layers were separated and the organic layer was washed twice with water (emulsion), dried over sodium sulfate and concentrated to give 8.6 g of a dark solid as residue. The solid was chromatographed on 180 g of silica gel eluting with 2% acetone in benzene and 5.8 g (80%) of solid was obtained from the eluant. An analytical sample, m.p. 107°-109° C. was prepared by recrystallizing with 2-propanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 2.5 hr
  3. temperatureThe solution was cooled
  4. customThe layers were separated
  5. washthe organic layer was washed twice with water (emulsion)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4d4f6b9eb746494e8e8e268466d04d64
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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