Acetyl chloride → HCID 19349925, compound

HRID 1672794Notes

Reaction equation

HRID 1672794 reaction equation
[OH:1][N:2]=[C:3]([NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([I:10])[CH:5]=1.[C:12](Cl)(=O)[CH3:13]>N1C=CC=CC=1.C(OCC)(=O)C>[I:10][C:6]1[CH:5]=[C:4]([C:3]2[N:11]=[C:12]([CH3:13])[O:1][N:2]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 4423571453565-59-8

Product 1

HCID 19349925HCID 19349925, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

N′-Hydroxy-3-iodobenzamidine (1.80 g, 6.87 mmol) obtained in Step 1 was dissolved in pyridine (14 mL), and the mixture was stirred at room temperature for 1 hour after adding acetyl chloride (0.551 mL, 6.87 mmol). The mixture was cooled to room temperature after further stirring at 90° C. for 4 hours. After diluting the mixture with ethyl acetate, the organic layer was washed with 1 mol/L hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate. The residue obtained upon concentration under reduced pressure was then purified by silica gel column chromatography to give 3-(3-iodophenyl)-5-methyl-1,2,4-oxadiazole (756 mg, 39%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. stirringafter further stirring at 90° C. for 4 hours
  3. washthe organic layer was washed with 1 mol/L hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained upon concentration under reduced pressure
  6. customwas then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-035e42d46afd4f1495ddc3813c4c0acd
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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