Sodium Hydroxide → HCID 131728621, compound

HRID 254260Notes

Reaction equation

HRID 254260 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[O:14][CH:13]=[N:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH-].[Na+]>[Zn].C(O)(C(F)(F)F)=O>[O:14]1[C:10]([C:6]2[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=2)=[CH:11][N:12]=[CH:13]1.[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 27370675-(3-Nitrophenyl)oxazole

Product 1

HCID 131728621HCID 131728621, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

1 g (5.26 mmol, 1 eq.) of 5-(3-nitrophenyl)oxazole and 10 mL of TFA are introduced into a 1 L flask. 1 g of zinc is carefully added in a plurality of batches. The mixture is stirred for 2 hours at room temperature then is poured over ice. Sodium hydroxide is slowly added until the medium becomes basic, and the medium is extracted with diethyl ether. The organic phase is washed with a 1 M solution of HCl and the impurities are extracted with diethyl ether. The aqueous phase is again basified with sodium hydroxide and the product is extracted with diethyl ether. The organic phases are combined, dried over MgSO4 and filtered. After concentration to dryness, 700 mg (yield=83%) of aniline 3-oxazol-5-yl-phenylamine are obtained, in the form of a beige solid. The product is used without subsequent purification.

Workup

  1. additionthen is poured over ice
  2. extractionthe medium is extracted with diethyl ether
  3. washThe organic phase is washed with a 1 M solution of HCl
  4. extractionthe impurities are extracted with diethyl ether
  5. extractionthe product is extracted with diethyl ether
  6. dry with materialdried over MgSO4
  7. filtrationfiltered

Sources & evidence

ORD record
ord-d8a88f9123b34ed9afbeef6fc4fe6f17
Source dataset
uspto-grants-2011_01
Patent number
US07875609B2

Reaction notes

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