Potassium Cyanide → HCID 19420771, compound

HRID 1734691Notes

Reaction equation

HRID 1734691 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 3x, 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 3x
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated to dryness
  4. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-004e3cb8d2a94c8c85589285c1f75288
Source dataset
uspto-grants-1996_07
Patent number
US05534532

Reaction notes

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