Sodium Cyanide → (5-Phenylisoxazol-3-yl)acetonitrile

HRID 1175607Notes

Reaction equation

HRID 1175607 reaction equation
CS(O[CH2:6][C:7]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:9][N:8]=1)(=O)=O.[C-:18]#[N:19].[Na+]>CS(C)=O.CCOC(C)=O>[C:12]1([C:10]2[O:9][N:8]=[C:7]([CH2:6][C:18]#[N:19])[CH:11]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 23159221HCID 23159221, compound

Product 1

HCID 33676789(5-Phenylisoxazol-3-yl)acetonitrileYield 110.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (5-phenylisoxazol-3-yl)methyl methanesulfonate (example 33d) (261 mg, 1.03 mmol) in anhydrous DMSO (8 mL) was added NaCN (252 mg, 5.15 mmol). The reaction mixture was heated at 80° C. under N2 for 15 hours, then diluted with EtOAc and washed with H2O (5×). The combined organic layers were dried over MgSO4, filtered and concentrated to yield a yellow solid (209 mg, 40%). 1H NMR (DMSO-d6, 400 MHz): 4.30 (s, 2H), 7.12 (s, 1H), 7.55-7.57 (m, 3H), 7.89-7.92 (m, 2H).

Workup

  1. washwashed with H2O (5×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-81a6da42384d4ccf982b274dfe6ea573
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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