Acetic Acid → 2-(1,3-Benzoxazol-2-yl)acetonitrile

HRID 2261634Notes

Reaction equation

HRID 2261634 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(O)(=O)C.C(#N)[CH:14]([CH2:16][C:17]#[N:18])O>C(O)C.C(Cl)Cl>[O:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:14]1[CH2:16][C:17]#[N:18]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 58012-AminophenolHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 8433252-(1,3-Benzoxazol-2-yl)acetonitrileYield 71.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-aminophenol (5.0 g, 45.8 mmol) dissolved in 115 mL of anhydrous ethanol and 8 mL of glacial acetic acid was added malonitrile (9.08 g, 140 mmol) at 100° C. The resulting homogeneous solution was refluxed for 24 hours and the solvent was removed in vacuo to yield a red/brown oil. The oil was diluted with CH2Cl2 (100 mL) and any remaining solids were then removed by filtration. The mother liquor was washed twice with a saturated sodium bicarbonate solution and twice with water, dried over magnesium sulfate, filtered and evaporated to yield 5.2 g (71%) of the product as a yellow oil. This material was used in the subsequent reaction without further purification.

Workup

  1. temperatureThe resulting homogeneous solution was refluxed for 24 hours
  2. customthe solvent was removed in vacuo
  3. customto yield a red/brown oil
  4. customany remaining solids were then removed by filtration
  5. washThe mother liquor was washed twice with a saturated sodium bicarbonate solution and twice with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-af91076e1d974c6d8d69d8217d370d08
Source dataset
uspto-grants-2010_12
Patent number
US07847101B2

Reaction notes

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