Sulfuric Acid → HCID 67350132, compound

HRID 1672820Notes

Reaction equation

HRID 1672820 reaction equation
S(=O)(=O)(O)O.[I:6][C:7]1[CH:8]=[C:9]([CH:17]=[CH:18][CH:19]=1)[C:10]([NH:12][CH2:13][C:14](=[O:16])[CH3:15])=O.[OH-].[Na+]>O>[I:6][C:7]1[CH:8]=[C:9]([C:10]2[O:16][C:14]([CH3:15])=[CH:13][N:12]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 64996782HCID 64996782, compound

Product 1

HCID 67350132HCID 67350132, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Concentrated sulfuric acid (13 mL) was added to 3-iodo-N-(2-oxopropyl)benzamide (1.33 g, 4.39 mmol) obtained in Step 2, and the mixture was stirred at 100° C. for 1.5 hours. The mixture was poured into iced water, neutralized with a 4 mol/L aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give 2-(3-iodophenyl)-5-methyl-1,3-oxazole (1.20 g, 96%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-178f1dcaf7c8493aa94d4ca73e2f5598
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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