Nitric Acid → 4-(4-Nitrophenyl)oxazole

HRID 1910746Notes

Reaction equation

HRID 1910746 reaction equation
[C:1]1([C:7]2[N:8]=[CH:9][O:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[N:8]=[CH:9][O:10][CH:11]=2)=[CH:6][CH:5]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5892794-Phenyl-1,3-oxazole

Product 1

HCID 145677974-(4-Nitrophenyl)oxazoleYield 42%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-Phenyloxazole (1 g, 6.89 mmol) was dissolved in concentrated sulfuric acid (5 mL) at 0° C. A cold solution of nitrating mixture (prepared by adding 3 mL conc. nitric acid to 5 mL of ice-cold conc. sulfuric acid) was added over 10 minutes. The mixture was allowed to warm to r.t. and stirred for 1 h. The resulting solution was poured into ice-cold water giving a white precipitate, which was filtered and washed thoroughly with water. The solid was dissolved in DCM and washed with water then brine. The organic phase was dried over sodium sulfate and concentrated to yield 4-(4-nitro-phenyl)-oxazole (550 mg, 42%) as a white solid.

Workup

  1. additionwas added over 10 minutes
  2. additionThe resulting solution was poured into ice-cold water giving a white precipitate, which
  3. filtrationwas filtered
  4. washwashed thoroughly with water
  5. dissolutionThe solid was dissolved in DCM
  6. washwashed with water
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ffd008174f1c460f823e039a0141c6bd
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

Loading…