4-Aminobenzoic Acid → 4-(5-Methyl-benzooxazol-2-yl)-phenylamine

HRID 855990Notes

Reaction equation

HRID 855990 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.[NH2:10][C:11]1[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=1>O>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:15]([C:14]3[CH:18]=[CH:19][C:11]([NH2:10])=[CH:12][CH:13]=3)=[N:1][C:2]=2[CH:3]=1

Participants

4

Reactant 2

HCID 9784-Aminobenzoic AcidHCID 72642-Amino-4-methylphenol

Product 1

HCID 3501894-(5-Methyl-benzooxazol-2-yl)-phenylamineYield 90.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 2-amino-p-cresol (1.5 g, 12 mmol), 4-aminobenzoic acid (1.67 g, 12 mmol) and 40 g polyphosphoric acid was heated at 190° C. under nitrogen for 6 h. The reaction mixture was cooled to room temperature and 300 ml water was added to the viscous liquid. The solid that precipitated was collected by filtration and dissolved in 200 ml ethyl acetate. The ethyl acetate solution was washed sequentially with 100 ml saturated aqueous sodium bicarbonate solution, 100 ml water and 100 ml brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure to yield the title compound as an off-white solid (2.43 g, 89% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solid that precipitated
  3. filtrationwas collected by filtration
  4. dissolutiondissolved in 200 ml ethyl acetate
  5. washThe ethyl acetate solution was washed sequentially with 100 ml saturated aqueous sodium bicarbonate solution, 100 ml water and 100 ml brine
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-deb486d19a7f4536b7d7bd7bbc7ac623
Source dataset
uspto-grants-2007_08
Patent number
US07262318B2

Reaction notes

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