Potassium Cyanide → HCID 19420771, compound

HRID 863855Notes

Reaction equation

HRID 863855 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.[C-:18]#[N:19].[K+]>C1COCC1.CS(C)=O.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][C:18]#[N:19])=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Product 1

HCID 19420771HCID 19420771, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(benzoxazol-2-yl)benzyl bromide (0.5 g; 1.7 mmol) in THF (3 ml) and DMSO (3 ml) is added potassium cyanide (0.22 g; 3.4 mmol) and the reaction is stirred for 72 hours. The reaction is diluted with CH2Cl2, washed with H2O 3×, dried (MgSO4) and concentrated to dryness. The residue is purified by column chromatography using methylene chloride to yield 4-(benzoxazol-2-yl)-benzyl cyanide which is used directly in Step D.

Workup

  1. washwashed with H2O 3×
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-794ea05dea734bf8bb5aca49e6e122ce
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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