Sodium Cyanide → HCID 69099717, compound

HRID 2251567Notes

Reaction equation

HRID 2251567 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]3[CH2:15][CH2:14]3)[O:11][CH:12]=2)=[CH:4][CH:3]=1.[Cu](C#N)[C:17]#[N:18].[C-]#N.[Na+]>CN1C(=O)CCC1>[CH:13]1([C:10]2[O:11][CH:12]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:17]#[N:18])=[CH:3][CH:4]=3)[N:9]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 59643131HCID 59643131, compoundHCID 178418260HCID 178418260, compound

Product 1

HCID 69099717HCID 69099717, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 4-(4-bromophenyl)-2-cyclopropyl-1,3-oxazole (1.78 g, 6.74 mmol) in NMP (25 mL) was added copper cyanide (4.22 g, 47.12 mmol). The mixture was heated to 185C for 4 h. Upon cooling, the mixture was poured into a 0C solution of 5% aqueous sodium cyanide (60 ml). The aqueous phase was extracted with Et2O. The combined organic phases were washed with, 5% aqueous sodium cyanide, water, and brine, dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (CH2Cl2/Hexanes, 2:3 to 10:0) to yield 4-(2-cyclopropy-1,3-oxazol-4-yl)benzonitrile as a yellow solid (1.00 g, 71%).

Workup

  1. temperatureUpon cooling
  2. extractionThe aqueous phase was extracted with Et2O
  3. washThe combined organic phases were washed with, 5% aqueous sodium cyanide, water, and brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (CH2Cl2/Hexanes, 2:3 to 10:0)

Sources & evidence

ORD record
ord-b26e69a093cc4989b38baf6edfae85cf
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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