Sodium Cyanide → 2-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile

HRID 1397399Notes

Reaction equation

HRID 1397399 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH:13]=O)[N:12]=2)=[CH:4][CH:3]=1.Cl.[CH3:16][NH:17][CH3:18].[C-:19]#[N:20].[Na+]>C1COCC1.CO.O>[CH3:16][N:17]([CH3:18])[CH:13]([C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[O:9][CH:10]=1)[C:19]#[N:20]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 10473Dimethylamine, hydrochlorideHCID 218062352-(4-Fluoro-phenyl)-oxazole-4-carbaldehyde

Product 1

HCID 673252862-(Dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrileYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(4-Fluorophenyl)oxazole-4-carbaldehyde (1.0 g, 5.23 mmol) was dissolved in THF-MeOH (20 mL, 1:1 v/v). This solution was added to a solution of dimethylamine hydrochloride (470 mg, 5.7 mmol) and NaCN (640 mg, 13.0 mmol) in water. The resulting reaction mixture was stirred at room temperature for 2 h, and then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 2-(dimethylamino)-2-(2-(4-fluorophenyl)oxazol-4-yl)acetonitrile (1.0 g, crude) as a brown oil, which was used without further purification. MS (ESI) m/z: Calculated for C13H12FN3O: 245.10. found: 245.9 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01d021e1c29c4e0287e929b2644bd438
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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