Sodium Cyanide → HCID 20477989, compound

HRID 2170226Notes

Reaction equation

HRID 2170226 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[Na+].[Cl-].[NH4+:20].[OH-].[NH4+]>CO>[NH2:20][CH:10]([C:9]1[CH:12]=[CH:13][CH:14]=[CH:15][C:8]=1[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 88060o-Phenoxybenzaldehyde

Product 1

HCID 20477989HCID 20477989, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-phenoxybenzaldehyde (1.0 g, 5.04 mmol) in methanol (10 mL) was added to a solution of sodium cyanide (0.297 g, 6.05 mmol) and ammonium chloride (0.494 g, 9.23 mmol) in ammonium hydroxide (10 mL, 85 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was concentrated by rotary evaporation. The residue was taken up in water and extracted with dichloromethane (2×). The combined organics were washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes) to provide the title compound (1.065 g, 94% yield).

Workup

  1. concentrationThe reaction mixture was concentrated by rotary evaporation
  2. extractionextracted with dichloromethane (2×)
  3. washThe combined organics were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2f12a186b57942019ecbb05d3ae86613
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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