Sodium Cyanide → HCID 67324194, compound

HRID 1397343Notes

Reaction equation

HRID 1397343 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][N:10]=1>CCO>[C:11]1([C:8]2[S:7][C:6]([CH2:5][C:1]#[N:2])=[N:10][CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 67324904HCID 67324904, compound

Product 1

HCID 67324194HCID 67324194, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

NaCN (0.46 g, 9.4 mmol) was added to a solution of 2-(bromomethyl)-5-phenylthiazole (2.0 g, 7.87 mmol) in dry EtOH (10 mL). The resulting reaction mixture was stirred at 70° C. for 2 h and then concentrated under reduced pressure, and diluted with ethyl acetate. The organic layer was 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 10% EtOAc in petroleum ether) to afford 2-(5-phenylthiazol-2-yl)acetonitrile (350 mg, yield 22%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1H), 7.56-7.54 (m, 2H), 7.46-7.40 (m, 3H), 4.15 (s, 2H). MS (ESI) m/z: Calculated for C11H8N2S: 200.04. found: 201.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was 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 10% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-31b53c44be174dcdb43bceb1a4f436b3
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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