Formamide → 4-(Oxazol-4-yl)benzonitrile

HRID 1436439Notes

Reaction equation

HRID 1436439 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[CH:13]([NH2:15])=[O:14]>O>[O:14]1[CH:2]=[C:3]([C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[N:15]=[CH:13]1

Participants

4

Reactant 2

HCID 713FormamideHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 223795804-(Oxazol-4-yl)benzonitrileYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

4-(2-Bromo-acetyl)-benzonitrile (1.2 g, 5.4 mmol) was dissolved in formamide (10 mL) and heated to 110° C. for 72 h. The mixture was cooled, diluted with water and extracted five times with methylene chloride. The organics were combined, washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (5%-10% acetone in hexane) afforded 4-(1,3-oxazol-4-yl)benzonitrile (0.16 g, 17%) as a white solid. Analytical HPLC: purity 100% at 270 nm, 6.8 min; 100% at 210-370 nm, 6.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted five times with methylene chloride
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ac8d02057f434e9dad91f92bbdd277bd
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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