4-Nitrobenzaldehyde → 5-(4-Nitrophenyl)-1,3-oxazole

HRID 2212577Notes

Reaction equation

HRID 2212577 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1)([O-:5])=[O:4].CC1C=CC(S([CH2:24][N+:25]#[C-:26])(=O)=O)=CC=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:10]2[O:11][CH:26]=[N:25][CH:24]=2)=[CH:12][CH:13]=1)([O-:5])=[O:4]

Participants

6

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 14798Sodium HydroxideHCID 161915Tosylmethyl isocyanide

Product 1

HCID 27370685-(4-Nitrophenyl)-1,3-oxazoleYield 144.8%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an aqueous solution containing 0.84 g of sodium hydroxide were added 0.45 g of 4-nitrobenzaldehyde, 12.2 g of a methylene chloride solution containing 0.65 g of TosMIC which was obtained in the same way as that of Example 6 and 0.10 g of tetrabutyl ammonium bromide at room temperature. The mixture was allowed to react at room temperature until HPLC found no trace of the starting materials. Upon the completion of the reaction, the reaction solution was washed with water and dried over anhydrous magnesium sulfate. The solvents were distilled off. An HPLC analysis showed that the concentrated residue contained 0.82 g of the target compound (yield: 93%).

Workup

  1. customto react at room temperature until HPLC
  2. customUpon the completion of the reaction
  3. washthe reaction solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvents were distilled off

Sources & evidence

ORD record
ord-e0beb0cf32294d93a12076674dc18816
Source dataset
uspto-grants-2006_09
Patent number
US07102010B2

Reaction notes

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