Acetic Acid → 5-Methyl-2-(4-nitrophenyl)oxazole

HRID 880489Notes

Reaction equation

HRID 880489 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([C:8]([NH:10][CH2:11][C:12]#[CH:13])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].C(O)(=O)C>C(O)C>[CH3:13][C:12]1[O:9][C:8]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=2)=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 3016782Benzamide, 4-nitro-N-2-propynyl-

Product 1

HCID 445506455-Methyl-2-(4-nitrophenyl)oxazoleYield 46.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
52.5 °C

Procedure

To a stirred solution of 4-nitro-N-prop-2-ynyl-benzamide (7.5 g, 36.7 mmol) in ethanol (150 mL) was added a solution of potassium hydroxide (4.1 g, 73.4 mmol) in ethanol (100 mL) and the mixture was stirred at 50-55° C. for 12 h. The mixture was acidified with acetic acid and concentrated to dryness in vacuo at 45-50° C. The resultant residue was extracted into ethyl acetate and the separated organic phase was washed with water; aqueous sodium bicarbonate, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 5-methyl-2-(4-nitrophenyl)oxazole (3.47 g, 46%) as an oil.

Workup

  1. concentrationconcentrated to dryness in vacuo at 45-50° C
  2. extractionThe resultant residue was extracted into ethyl acetate
  3. washthe separated organic phase was washed with water
  4. dry with materialaqueous sodium bicarbonate, brine, dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f22c9d01cbe4ef58247bbea52653ef0
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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