Benzoic Acid → 6-nitro-2-phenyl-1,3-benzoxazole

HRID 2243104Notes

Reaction equation

HRID 2243104 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1O.[OH-].[Na+]>O>[C:2]1([C:1]2[O:9][C:16]3[CH:15]=[C:14]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:12][C:11]=3[N:10]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 14798Sodium HydroxideHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 30929366-nitro-2-phenyl-1,3-benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
117.5 °C

Procedure

PPA (160 g) is added to benzoic acid (14.26 g, 0.117 mol) and 2-amino-5-nitrophenol (20 g, 0.117 mol). The mixture is heated at 115-120° C. for 30 minutes and cooled, and water (200 ml) is added dropwise, followed by addition of 32% NaOH (pH=10). The product is filtered off, washed with water and filtered off. It is recrystallized from isopropyl ether. Yield: 25 g (90%); Elem. anal. C13H8N2O3; theory C, 65.00; H, 3.35; N, 11.66. found C, 64.56; H, 3.22; N, 11.43. IR (KBr): 1551, 1515, 1340 cm−1.

Workup

  1. temperaturecooled
  2. filtrationThe product is filtered off
  3. washwashed with water
  4. filtrationfiltered off
  5. customIt is recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-ed220ddc4ac3469185c645d478507bb1
Source dataset
uspto-grants-2010_03
Patent number
US07674809B2

Reaction notes

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