Sodium Cyanide → HCID 21180547, compound

HRID 1386441Notes

Reaction equation

HRID 1386441 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]1[O:21][C:20]2[CH:19]=[CH:18][C:8]([O:9][CH:10](Cl)[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:7][C:6]=2[O:5]1>CN(C=O)C>[CH2:4]1[O:21][C:20]2[CH:19]=[CH:18][C:8]([O:9][C:14]3[CH:15]=[CH:16][CH:11]=[C:10]([O:9][C:8]4[CH:18]=[CH:19][C:20]5[O:21][CH2:4][O:5][C:6]=5[CH:7]=4)[C:13]=3[CH2:12][C:1]#[N:2])=[CH:7][C:6]=2[O:5]1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86583624HCID 86583624, compound

Product 1

HCID 21180547HCID 21180547, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium cyanide (85 mg, 1.6 mmol) was added to a solution of 2,6-bis-[(3,4-(methylenedioxy)phenoxy]-benzyl chloride (435 mg, 1.1 mmol) in DMF (3 ml) at room temperature. The resulting dark brown solution was stirred at room temperature for 18 hours. The DMF was removed under high vacuum and the remaining brown residue was extracted into ethyl acetate and washed with brine (1×5 ml). After drying over MgSO4, the solvent was removed by evaporation and the remaining solid was purified by column chromatography using 10% ethyl acetate-hexanes which yielded 217 mg (51% yield) of the pure benzyl cyanide as a white powder.

Workup

  1. customThe DMF was removed under high vacuum
  2. extractionthe remaining brown residue was extracted into ethyl acetate
  3. washwashed with brine (1×5 ml)
  4. dry with materialAfter drying over MgSO4
  5. customthe solvent was removed by evaporation
  6. customthe remaining solid was purified by column chromatography

Sources & evidence

ORD record
ord-4a96fcc6932d45f7a2113b7690e8caeb
Source dataset
uspto-grants-2001_07
Patent number
US06265428B1

Reaction notes

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