Benzoic Acid → 2-phenyl-1,3-benzoxazol-5-amine

HRID 1896738

Reaction equation

Cl.Cl.[NH2:3][C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[OH:11].[C:12](O)(=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O>[C:13]1([C:12]2[O:11][C:5]3[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=3[N:3]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 180 °C

Procedure

To polyphosphoric acid at 110° C. were added simultaneously 2,4-diaminophenol dihydrochloride (7.88 g, 40 mmol) and benzoic acid (4.88 g, 40 mmol). The resulting mixture was then heated to 180° C. for 3 h. The solution was then poured into water. The resulting precipitate was collected by filtration and washed with saturated sodium bicarbonate solution. The crude product was recrystallised from ethanol/water to afford 8.15 g (97%) of the title compound (LCMS RT=5.17 min, MH+ 211.1)

Workup

filtrationThe resulting precipitate was collected by filtration
washwashed with saturated sodium bicarbonate solution
customThe crude product was recrystallised from ethanol/water

Sources & evidence

ORD record: ord-6b8a684af1a24d0a815520d09caf1cfb
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518980B2

Linked notes

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