Potassium Carbonate → HCID 22493295, compound

HRID 1816302Notes

Reaction equation

HRID 1816302 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O-:3])=[O:2].C1(C)C=CC(S([CH2:22][N+:23]#[C-:24])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[N+:1]([C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[C:6]1[O:7][CH:24]=[N:23][CH:22]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 796744-Chloro-2-nitrobenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 22493295HCID 22493295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-nitro-4-chlorobenzaldehyde (2.2 g, 11.8 mmol) and p-toluenesulfonyl-methylisocyanide (2.8 g, 14.2 mmol) in methanol (50 mL) was added potassium carbonate (8.2 g, 59 mmol) solid. The heterogeneous mixture was heated to reflux for 2.5 hours. Upon moving to room temperature, the reaction was filtered and concentrated in vacuo. The residue was dissolved in 0.1N sodium hydroxide and extracted with methylene chloride two times. The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to give crude 5-(2-nitro-4-chlorophenyl)oxazole.

Workup

  1. temperatureThe heterogeneous mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. customUpon moving to room temperature
  4. filtrationthe reaction was filtered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 0.1N sodium hydroxide
  7. extractionextracted with methylene chloride two times
  8. dry with materialThe combined organics were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f55a6d089241af914759a4863f558d
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

Loading…