Potassium Cyanide → HCID 67325210, compound

HRID 1397374Notes

Reaction equation

HRID 1397374 reaction equation
[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][CH:7]=1>CN(C=O)C>[C:11]1([C:9]2[S:10][C:6]([CH2:5][C:1]#[N:2])=[CH:7][N:8]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 67324761HCID 67324761, compound

Product 1

HCID 67325210HCID 67325210, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

KCN (154 mg, 2.36 mmol) was added to a solution of 5-(bromomethyl)-2-phenylthiazole (400 mg, 1.57 mmol) in dry DMF (10 mL). The resulting reaction mixture was stirred at room temperature for 10 h. The mixture was then quenched with water and the organic product was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20% EtOAc in petroleum ether) to afford 2-(2-phenylthiazol-5-yl)acetonitrile (230 mg, yield 73%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.94-7.90 (m, 2H), 7.76 (s, 1H), 7.47-7.45 (m, 3H), 3.98 (d, J=1.1 Hz, 2H). MS (ESI) m/z: Calculated for C11H8N2S: 200.05. found: 201.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customThe mixture was then quenched with water
  3. extractionthe organic product was extracted with EtOAc
  4. washThe combined extracts were washed with H2O and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-d869cb0e1cf44c98a7d1ec802ea068bd
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

Loading…