Benzaldehyde → 5-Chloro-6-nitro-2-phenyl-1,3-benzoxazole

HRID 605309Notes

Reaction equation

HRID 605309 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C>>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]2[O:12][C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:1][C:2]=2[CH:7]=1

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 297MethaneHCID 38948482-Amino-4-chloro-5-nitrophenol

Product 1

HCID 136092465-Chloro-6-nitro-2-phenyl-1,3-benzoxazole

Procedure

To a flask equipped with a vigreux column was added 2-amino-4-chloro-5-nitro-phenol, benzaldehyde, Darco KB and xylenes. The mixture was then refluxed overnight and the mixture was cooled, filtered and the solvent removed under vacuum. The resultant solid was recrystallized from Et2O to yield 5-chloro-6-nitro-2-phenyl-benzooxazole which was subjected to the procedure from Example 349B substituting 5-chloro-6-nitro-2-phenyl-benzooxazole for the product from Example 349A to provide the title product.

Workup

  1. customTo a flask equipped with a vigreux column
  2. temperatureThe mixture was then refluxed overnight
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe resultant solid was recrystallized from Et2O

Sources & evidence

ORD record
ord-4eeaa7693a61453aa658627e4146e84c
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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