Potassium Cyanide → HCID 16789189, compound

HRID 81511Notes

Reaction equation

HRID 81511 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH4+:11].[Cl-].[C-:13]#[N:14].[K+]>N>[NH2:11][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:9])[C:13]#[N:14]

Participants

5

Reactant 3

HCID 9032Potassium CyanideHCID 165023'-BromoacetophenoneHCID 25517Ammonium Chloride

Product 1

HCID 16789189HCID 16789189, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

A mixture of 1-(3-bromo-phenyl)-ethanone (10 g, 50 mmol), NH4Cl (6.4 g, 100 mmol) and KCN (6.5 g, 100 mmol) was dissolved in ammonia (200 ml). The solution was stirred at room temperature for 3 days. The mixture was extracted with diethylether (3×300 ml). The organic phase was washed with water and brine, dried with Na2SO4 and concentrated in vacuo to yield the title compound (also containing some unreacted starting material). 11H-NMR (400 MHz, CDCl3): 7.84 (s, 1H), 7.59 (d, 1H), 7.48 (d, 1H), 7.28 (m, 1H), 1.75 (s, 3H).

Workup

  1. extractionThe mixture was extracted with diethylether (3×300 ml)
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-259704096c394995a07b89c12bbf9a6c
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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