Water → HCID 14835352, compound

HRID 1198986Notes

Reaction equation

HRID 1198986 reaction equation
Br[CH2:2][C:3]1[CH:17]=[CH:16][C:6]2=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:8][N:9]=[C:5]2[CH:4]=1.[C-:18]#[N:19].[K+].O1CCOCC1.O>C(Cl)Cl>[C:10]1([C:7]2[O:8][N:9]=[C:5]3[CH:4]=[C:3]([CH2:2][C:18]#[N:19])[CH:17]=[CH:16][C:6]=23)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 312751,4-DioxaneHCID 14835351HCID 14835351, compound

Product 1

HCID 14835352HCID 14835352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10.9 g (0.038 mole) of slightly impure 6-(bromomethyl)-3-phenyl-2,1-benzisoxazole, 9.8 g (0.15 mole) of potassium cyanide, 80 ml of dioxane, and 50 ml of water was heated at reflux under a nitrogen atmosphere for 2.5 hr. The mixture was diluted with 200 ml of methylene chloride and the layers were separated. The organic layer was washed twice with water, once with brine, and dried over sodium sulfate, and concentrated to give 7.5 g of gray solid as residue. The solid was chromatographed on 150 g of silica gel and the title compound was eluted with 1% methanol in benzene to yield 3.3 g (37%) of product, m.p. 148°-155° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 2.5 hr
  3. customthe layers were separated
  4. washThe organic layer was washed twice with water, once with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-205217c1e3394797849eafa50f0d9ac9
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

Loading…