Potassium Carbonate → 3-(1,3-oxazol-5-yl)benzoic Acid

HRID 860411Notes

Reaction equation

HRID 860411 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])=[O:2].C1(C)C=CC(S([CH2:21][N+:22]#[C-:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:2]1[C:1]([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=2)[C:6]([OH:8])=[O:7])=[CH:23][N:22]=[CH:21]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120773-CarboxybenzaldehydeHCID 161915Tosylmethyl isocyanide

Product 1

HCID 71278133-(1,3-oxazol-5-yl)benzoic AcidYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-formylbenzoic acid (500 mg) and p-toluenesulfonylmethyl isocyanide (715 mg) in methanol (20 mL) was added potassium carbonate (1.38 g) and the mixture was heated under reflux for 2 hours. After evaporation of solvent, the residue was partitioned between ethyl acetate and water. The aqueous layer was separated and acidified with 1N hydrochloric acid. The resulting precipitates were collected and washed with water, methanol and ether to give 3-(1,3-oxazol-5-yl)benzoic acid as a colorless amorphous powder (484 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter evaporation of solvent
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe aqueous layer was separated
  6. customThe resulting precipitates
  7. customwere collected
  8. washwashed with water, methanol and ether

Sources & evidence

ORD record
ord-4e042cf889b546b1be76e1dde12bf7a0
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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