Ethyl Acetate → 2-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazole

HRID 2373452Notes

Reaction equation

HRID 2373452 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.[C:11]([NH:14][NH2:15])(=O)[CH3:12].CCOC(C)=O>O=P(Cl)(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[O:8][C:11]([CH3:12])=[N:14][N:15]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 120854-Iodobenzoic acidHCID 14039Acetohydrazide

Product 1

HCID 6765692-(4-Iodophenyl)-5-methyl-[1,3,4]oxadiazoleYield 31.9%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-iodobenzoic acid (1.0 g) and acethydrazide (329 mg) in POCl3 (4 ml) is stirred over night at 80° C., then another day at 100° C. AcOEt (50 ml) is added and the mixture is washed with H2O (50 ml), sat. aq. Na2CO3 sol. (50 ml) and H2O (50 ml). After drying over Na2SO4 the solvent is evaporated and the product is purified by flash chromatography (silica gel, CH2Cl2/MeOH/25% aq. NH4OH 90:9:1). 368 mg of 2-(4-iodo-phenyl)-5-methyl-[1,3,4]oxadiazole (19) are obtained as a yellowish solid, MS (ESI) 287.0 (M+H)+.

Workup

  1. customat 100° C
  2. washthe mixture is washed with H2O (50 ml), sat. aq. Na2CO3 sol. (50 ml) and H2O (50 ml)
  3. dry with materialAfter drying over Na2SO4 the solvent
  4. customis evaporated
  5. customthe product is purified by flash chromatography (silica gel, CH2Cl2/MeOH/25% aq. NH4OH 90:9:1)

Sources & evidence

ORD record
ord-9c6b46e94b304bd49a92d3cf0408f08b
Source dataset
uspto-grants-2008_12
Patent number
US07459480B2

Reaction notes

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