N-bromobutanimide → 5-(Bromomethyl)-2-methyl-4-phenyl-1,3-oxazole

HRID 350740Notes

Reaction equation

HRID 350740 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH3:13])[O:10][C:11]=2[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:12][C:11]1[O:10][C:9]([CH3:13])=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 599323Oxazole, 2,5-dimethyl-4-phenyl-

Product 1

HCID 132932915-(Bromomethyl)-2-methyl-4-phenyl-1,3-oxazoleYield 89%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-phenyl-2, 5-dimethyloxazole (6.21 g), N-bromosuccinimide (5.34 g), azobisisobutyronitrile (0.25 g) and carbon tetrachloride (90 mL) was stirred with heating under reflux for 15 min. The reaction mixture was cooled, washed successively with water, saturated aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethanol to give 5-bromomethyl-4-phenyl-2-methyloxazole (6.73 g, yield 78%) as colorless crystals. melting point: 75–76° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 min
  3. temperatureThe reaction mixture was cooled
  4. washwashed successively with water, saturated aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-bc8ca8adc1bd41dfb6b5a210570ab668
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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